No renderable structure data available
C1C2=C(C=CC=C2Br)NC(=O)O1Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 5-bromo-1,4-dihydro-3,1-benzoxazin-2-one |
|---|---|
| IUPAC Name | — |
| CAS Number | 861106-93-6 |
| Database ID | 18444520 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
5-bromo-1,4-dihydro-3,1-benzoxazin-2-one (CAS 861106-93-6) 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 18444520
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-3877ab8c9d58409d9089df2ac0edf7faConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-db5b1c906a0c4f008989c1810a5e85f3Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 5-bromo-1,4-dihydro-benzo[d][1,3]oxazin-2-one (96 mg, 0.42 mmol) and 1-Boc-piperazine (100 mg, 0.54 mmol) in 2 ml toluene was added to a mixture of Pd2(dba)3 (8 mg, 0.009 mmol), BINAP (13 mg, 0.022 mmol), NaOt-Bu (121 mg, 1.26 mmol). With stirring, the solution was heated at 95° C.-100° C. for 4 hours and was allowed to cool to room temperature. The reaction mixture was filtered through celite and washed with ethyl acetate. The filtrate was washed with water and brine. After drying over MgSO4, the organic fraction was concentrated in vacuo and the resulting brown residue was purified by prep TLC to give 43 mg 4-(2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-5-yl)-piperazine-1-carboxylic acid tert-butyl ester as a yellow solid (31%). the solution was heated at 95° C.-100° C. for 4 hours The reaction mixture was filtered through celite washed with ethyl acetate The filtrate was washed with water and brine After drying over MgSO4 the organic fraction was concentrated in vacuo the resulting brown residue was purified by prep TLC
Source ID: ord-39f2b9ad87414693a16c9ea290b0dd37Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of (2-Amino-6-bromo-phenyl)-methanol (549 mg, 2.72 mmol) and triphosgen (282 mg, 0.95 mmol) in THF (20 ml) was heated at 50° C. for an hours. After cooling to room temperature, the reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed by water and brine. After drying over MgSO4, the solution was concentrated under vacuum to give 5-bromo-1,4-dihydro-benzo[d][1,3]oxazin-2-one (582 mg, 94%) as a white solid. MS: 226.1 (M−H)−. the reaction mixture was partitioned between water and ethyl acetate The organic layer was washed by water and brine After drying over MgSO4 the solution was concentrated under vacuum
Source ID: ord-ab91484b3bca4409b8c3e72442086230Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 5-bromo-1,4-dihydro-benzo[d][1,3]oxazin-2-one (96 mg, 0.42 mmol) and 1-Boc-piperazine (100 mg, 0.54 mmol) in 2 ml toluene was added to a mixture of Pd2(dba)3 (8 mg, 0.009 mmol), BINAP (13 mg, 0.022 mmol), NaOt-Bu (121 mg, 1.26 mmol). With stirring, the solution was heated at 95° C.–100° C. for 4 hours and was allowed to cool to room temperature. The reaction mixture was filtered through celite and washed with ethyl acetate. The filtrate was washed with water and brine. After drying over MgSO4, the organic fraction was concentrated in vacuo and the resulting brown residue was purified by prep TLC to give 43 mg 4-(2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-5-yl)-piperazine-1-carboxylic acid tert-butyl ester as a yellow solid (31%). the solution was heated at 95° C.–100° C. for 4 hours The reaction mixture was filtered through celite washed with ethyl acetate The filtrate was washed with water and brine After drying over MgSO4 the organic fraction was concentrated in vacuo the resulting brown residue was purified by prep TLC
Source ID: ord-ecb4a00ad89e4aafb68bb986c4f86c0bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of (2-Amino-6-bromo-phenyl)-methanol (549 mg, 2.72 mmol) and triphosgen (282 mg, 0.95 mmol) in THF (20 ml) was heated at 50° C. for an hours. After cooling to room temperature, the reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed by water and brine. After drying over MgSO4, the solution was concentrated under vacuum to give 5-bromo-1,4-dihydro-benzo[d][1,3]oxazin-2-one (582 mg, 94%) as a white solid. MS: 226.1 (M−H)−. (M+H)−. the reaction mixture was partitioned between water and ethyl acetate The organic layer was washed by water and brine After drying over MgSO4 the solution was concentrated under vacuum
Source ID: ord-2c06167387b64c15aaf3ee646d30489aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of (2-Amino-6-bromo-phenyl)-methanol (549 mg, 2.72 mmol) and triphosgen (282 mg, 0.95 mmol) in THF (20 ml) was heated at 50° C. for an hours. After cooling to room temperature, the reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed by water and brine. After drying over MgSO4, the solution was concentrated under vacuum to give 5-bromo-1,4-dihydro-benzo[d][1,3]oxazin-2-one (582 mg, 94%) as a white solid. MS: 226.1 (M−H)−. (M+H)−. the reaction mixture was partitioned between water and ethyl acetate The organic layer was washed by water and brine After drying over MgSO4 the solution was concentrated under vacuum
Source ID: ord-2c06167387b64c15aaf3ee646d30489aConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-3877ab8c9d58409d9089df2ac0edf7faConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-db5b1c906a0c4f008989c1810a5e85f3Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 5-bromo-1,4-dihydro-benzo[d][1,3]oxazin-2-one (96 mg, 0.42 mmol) and 1-Boc-piperazine (100 mg, 0.54 mmol) in 2 ml toluene was added to a mixture of Pd2(dba)3 (8 mg, 0.009 mmol), BINAP (13 mg, 0.022 mmol), NaOt-Bu (121 mg, 1.26 mmol). With stirring, the solution was heated at 95° C.-100° C. for 4 hours and was allowed to cool to room temperature. The reaction mixture was filtered through celite and washed with ethyl acetate. The filtrate was washed with water and brine. After drying over MgSO4, the organic fraction was concentrated in vacuo and the resulting brown residue was purified by prep TLC to give 43 mg 4-(2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-5-yl)-piperazine-1-carboxylic acid tert-butyl ester as a yellow solid (31%). the solution was heated at 95° C.-100° C. for 4 hours The reaction mixture was filtered through celite washed with ethyl acetate The filtrate was washed with water and brine After drying over MgSO4 the organic fraction was concentrated in vacuo the resulting brown residue was purified by prep TLC
Source ID: ord-39f2b9ad87414693a16c9ea290b0dd37Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of (2-Amino-6-bromo-phenyl)-methanol (549 mg, 2.72 mmol) and triphosgen (282 mg, 0.95 mmol) in THF (20 ml) was heated at 50° C. for an hours. After cooling to room temperature, the reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed by water and brine. After drying over MgSO4, the solution was concentrated under vacuum to give 5-bromo-1,4-dihydro-benzo[d][1,3]oxazin-2-one (582 mg, 94%) as a white solid. MS: 226.1 (M−H)−. the reaction mixture was partitioned between water and ethyl acetate The organic layer was washed by water and brine After drying over MgSO4 the solution was concentrated under vacuum
Source ID: ord-ab91484b3bca4409b8c3e72442086230Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 5-bromo-1,4-dihydro-benzo[d][1,3]oxazin-2-one (96 mg, 0.42 mmol) and 1-Boc-piperazine (100 mg, 0.54 mmol) in 2 ml toluene was added to a mixture of Pd2(dba)3 (8 mg, 0.009 mmol), BINAP (13 mg, 0.022 mmol), NaOt-Bu (121 mg, 1.26 mmol). With stirring, the solution was heated at 95° C.–100° C. for 4 hours and was allowed to cool to room temperature. The reaction mixture was filtered through celite and washed with ethyl acetate. The filtrate was washed with water and brine. After drying over MgSO4, the organic fraction was concentrated in vacuo and the resulting brown residue was purified by prep TLC to give 43 mg 4-(2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-5-yl)-piperazine-1-carboxylic acid tert-butyl ester as a yellow solid (31%). the solution was heated at 95° C.–100° C. for 4 hours The reaction mixture was filtered through celite washed with ethyl acetate The filtrate was washed with water and brine After drying over MgSO4 the organic fraction was concentrated in vacuo the resulting brown residue was purified by prep TLC
Source ID: ord-ecb4a00ad89e4aafb68bb986c4f86c0bPubChem References
These sources are listed in the compound's public database record.
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