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CC(C)(CO)NC(=O)C1=CC=CC=C1Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | N-(1-hydroxy-2-methylpropan-2-yl)benzamide |
|---|---|
| IUPAC Name | — |
| CAS Number | 19312-05-1 |
| Database ID | 639965 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
N-(1-hydroxy-2-methylpropan-2-yl)benzamide (CAS 19312-05-1) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 639965
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-743c57ce1b4e4f79bff08f86b2dace6dConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To 40 ml of freshly distilled thionyl chloride at 0° was added in portions over 15 minutes was stirring 3.86 g (0.02 mol) 2-benzoylamino-2-methyl-1-propanol. The solution was warmed to room temperature and heated under reflux for 2 hours. The thionyl chloride was removed under reduced pressure to afford a yellow oil which crystallized at 0° following the addition of anhydrous ether. The solid was triturated in anhydrous ether overnight and isolated by filtration under a nitrogen atmosphere. After drying in vacuo over calcium sulfate, 2.00 g (0.009 mol), 45%, 2-phenyl-4,4-dimethyl-1,3-oxazoline hydrochloride was obtained as a white solid, mp 149°-151°; ir (KBr) 1640 (c=N) cm-1, pmr (D2O) δ 1.60 (s, 6H), 4.70 (s, 2H) and 7.3-8.2 (m, 5H) ppm. heated under reflux for 2 hours The thionyl chloride was removed under reduced pressure to afford a yellow oil which crystallized at 0° the addition of anhydrous ether The solid was triturated in anhydrous ether overnight isolated by filtration under a nitrogen atmosphere After drying in vacuo over calcium sulfate, 2.00 g (0.009 mol), 45%
Source ID: ord-e4a2ab70c0104f6f8aa39a7b7de746b5Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a 250 ml dichloromethane solution containing 89 g (1.0 mol) 2-amino-2-methyl-1-propanol at 0° was added dropwise with stirring 70 g (0.5 mol) benzoyl chloride in 250 ml dichloromethane. The reaction mixture was warmed to room temperature and stirred for several hours. The 2-amino-2-methyl-1-propanol hydrochloride was removed from the reaction mixture by filtration and was thoroughly washed with dichloromethane. The filtrate and washings were combined and the dichloromethane removed under reduced pressure to afford 67.55 g (0.35 mol), 70%, 2-benzoylamino-2-methyl-1-propanol as a white solid, mp 80°-82°, sublimation at 75° (0.2 mm); ir (KBr) 1630 (c=o) cm-1 ; pmr (CDCl3) δ 1.50 (s, 6H), 3.67 (s, 2H), 5.27 (bs, 1H), 6.92 (bs, 1H) and 7.1-8.3 (m, 5H) ppm. was added dropwise The 2-amino-2-methyl-1-propanol hydrochloride was removed from the reaction mixture by filtration was thoroughly washed with dichloromethane the dichloromethane removed under reduced pressure
Source ID: ord-dfce4f8b23a24a4db44efe712d86e5d6Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To 40 ml of freshly distilled thionyl chloride at 0° was added in portions over 15 minutes with stirring 3.86 g (0.02 mol) 2-benzoylamino-2-methyl-1-propanol. The solution was warmed to room temperature and heated under reflux for 2 hours. The thionyl chloride was removed under reduced pressure to afford a yellow oil which crystallized at 0° following the addition of anhydrous ether. The solid was triturated in anhydrous ether overnight and isolated by filtration under a nitrogen atmosphere. After drying in vacuo over calcium sulfate, 2.00 g (0.009 mol), 45%, 2-phenyl-4,4-dimethyl-1,3-oxazoline hydrochloride was obtained as a white solid, mp 149°-151°; ir (KBr) 1640 (c=N) cm-1, pmr (D2O) δ 1.60 (s, 6H), 4.70 (s, 2H) and 7.3-8.2 (m, 5H) ppm. heated under reflux for 2 hours The thionyl chloride was removed under reduced pressure to afford a yellow oil which crystallized at 0° the addition of anhydrous ether The solid was triturated in anhydrous ether overnight isolated by filtration under a nitrogen atmosphere After drying in vacuo over calcium sulfate, 2.00 g (0.009 mol), 45%
Source ID: ord-d109789e2c4c4e62aa9d6982ec1dc21dConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a 250 ml dichloromethane solution containing 89 g (1.0 mol) 2-amino-2-methyl-1-propanol at 0° was added dropwise with stirring 70 g (0.5 mol) benzoyl chloride in 250 ml dichloromethane. The reaction mixture was warmed to room temperature and stirred for several hours. The 2-amino-2-methyl-1-propanol hydrochloride was removed from the reaction mixture by filtration and was thoroughly washed with dichloromethane. The filtrate and washings were combined and the dichloromethane removed under reduced pressure to afford 67.55 g (0.35 mol), 70%, 2-benzoylamino-2-methyl-1-propanol as a white solid, mp 80°-82°, sublimation at 75° (0.2 mm); ir (KBr) 1630 (c=o) cm-1 ; pmr (CDCl3) δ 1.50 (s, 6H), 3.67 (s, 2H), 5.27 (bs, 1H), 6.92 (bs, 1H) and 7.1 - 8.3 (m, 5H) ppm. was added dropwise The 2-amino-2-methyl-1-propanol hydrochloride was removed from the reaction mixture by filtration was thoroughly washed with dichloromethane the dichloromethane removed under reduced pressure
Source ID: ord-952d3c8029414ad9a0aac26dfe0ae5c8Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a 250 ml dichloromethane solution containing 89 g (1.0 mol) 2-amino-2-methyl-1-propanol at 0° was added dropwise with stirring 70 g (0.5 mol) benzoyl chloride in 250 ml dichloromethane. The reaction mixture was warmed to roome temperature and stirred for several hours. The 2-amino-2-methyl-1-propanol hydrochloride was removed from the reaction mixture by filtration and was thoroughly washed with dichloromethane. The filtrate and washings were combined and the dichloromethane removed under reduced pressure to afford 67.55 g (0.35 mol), 70%, 2-benzoylamino-2-methyl-1-propanol as a white solid, mp 80°-82°, sublimation at 75° (0.2 mm); ir (KBr) 1630 (c=o) cm-1 ; pmr (CDCl3) δ 1.50 (s, 6H), 3.67 (s, 2H), 5.27 (bs, 1H), 6.92 (bs, 1H) and 7.1 - 8.3 (m, 5H) ppm. was added dropwise The reaction mixture was warmed The 2-amino-2-methyl-1-propanol hydrochloride was removed from the reaction mixture by filtration was thoroughly washed with dichloromethane the dichloromethane removed under reduced pressure
Source ID: ord-3d534a8e6e624c878b542cd2fafca52cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a 250 ml dichloromethane solution containing 89 g (1.0 mol) 2-amino-2-methyl-1-propanol at 0° was added dropwise with stirring 70 g (0.5 mol) benzoyl chloride in 250 ml dichloromethane. The reaction mixture was warmed to roome temperature and stirred for several hours. The 2-amino-2-methyl-1-propanol hydrochloride was removed from the reaction mixture by filtration and was thoroughly washed with dichloromethane. The filtrate and washings were combined and the dichloromethane removed under reduced pressure to afford 67.55 g (0.35 mol), 70%, 2-benzoylamino-2-methyl-1-propanol as a white solid, mp 80°-82°, sublimation at 75° (0.2 mm); ir (KBr) 1630 (c=o) cm-1 ; pmr (CDCl3) δ 1.50 (s, 6H), 3.67 (s, 2H), 5.27 (bs, 1H), 6.92 (bs, 1H) and 7.1 - 8.3 (m, 5H) ppm. was added dropwise The reaction mixture was warmed The 2-amino-2-methyl-1-propanol hydrochloride was removed from the reaction mixture by filtration was thoroughly washed with dichloromethane the dichloromethane removed under reduced pressure
Source ID: ord-3d534a8e6e624c878b542cd2fafca52cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Prepared as in Example 215c from N-(1-hydroxy-2-methylpropan-2-yl)benzamide (Boyd, R. N.; Hansen, R. H. J. Am. Chem. Soc. 1953, 75, 5896) and 2,6-dinitrobenzonitrile in 91% yield as a pale yellow solid. MS 340 (MH+).
Source ID: ord-a471328061164e9d985b366971eb705cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Prepared as in Example 215c from N-(1-hydroxy-2-methylpropan-2-yl)benzamide (Boyd, R. N.; Hansen, R. H. J. Am. Chem. Soc. 1953, 75, 5896) and 2,6-dinitrobenzonitrile in 91% yield as a pale yellow solid. MS 340 (MH+).
Source ID: ord-cb0bb413d78045b188939f12599ed077Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Prepared as in Example 215c from N-(1-hydroxy-2-methylpropan-2-yl)benzamide (Boyd, R. N.; Hansen, R. H. J. Am. Chem. Soc. 1953, 75, 5896) and 2,6-dinitrobenzonitrile in 91% yield as a pale yellow solid. MS 340 (MH+).
Source ID: ord-cb0bb413d78045b188939f12599ed077Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To 40 ml of freshly distilled thionyl chloride at 0° was added in portions over 15 minutes was stirring 3.86 g (0.02 mol) 2-benzoylamino-2-methyl-1-propanol. The solution was warmed to room temperature and heated under reflux for 2 hours. The thionyl chloride was removed under reduced pressure to afford a yellow oil which crystallized at 0° following the addition of anhydrous ether. The solid was triturated in anhydrous ether overnight and isolated by filtration under a nitrogen atmosphere. After drying in vacuo over calcium sulfate, 2.00 g (0.009 mol), 45%, 2-phenyl-4,4-dimethyl-1,3-oxazoline hydrochloride was obtained as a white solid, mp 149°-151°; ir (KBr) 1640 (c=N) cm-1, pmr (D2O) δ 1.60 (s, 6H), 4.70 (s, 2H) and 7.3-8.2 (m, 5H) ppm. heated under reflux for 2 hours The thionyl chloride was removed under reduced pressure to afford a yellow oil which crystallized at 0° the addition of anhydrous ether The solid was triturated in anhydrous ether overnight isolated by filtration under a nitrogen atmosphere After drying in vacuo over calcium sulfate, 2.00 g (0.009 mol), 45%
Source ID: ord-e4a2ab70c0104f6f8aa39a7b7de746b5Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To 40 ml of freshly distilled thionyl chloride at 0° was added in portions over 15 minutes was stirring 3.86 g (0.02 mol) 2-benzoylamino-2-methyl-1-propanol. The solution was warmed to room temperature and heated under reflux for 2 hours. The thionyl chloride was removed under reduced pressure to afford a yellow oil which crystallized at 0° following the addition of anhydrous ether. The solid was triturated in anhydrous ether overnight and isolated by filtration under a nitrogen atmosphere. After drying in vacuo over calcium sulfate, 2.00 g (0.009 mol), 45%, 2-phenyl-4,4-dimethyl-1,3-oxazoline hydrochloride was obtained as a white solid, mp 149°-151°; ir (KBr) 1640 (c=N) cm-1, pmr (D2O) δ 1.60 (s, 6H), 4.70 (s, 2H) and 7.3-8.2 (m, 5H) ppm. heated under reflux for 2 hours The thionyl chloride was removed under reduced pressure to afford a yellow oil which crystallized at 0° the addition of anhydrous ether The solid was triturated in anhydrous ether overnight isolated by filtration under a nitrogen atmosphere After drying in vacuo over calcium sulfate, 2.00 g (0.009 mol), 45%
Source ID: ord-e4a2ab70c0104f6f8aa39a7b7de746b5PubChem References
These sources are listed in the compound's public database record.
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