No renderable structure data available
O=C1COC2C(=CC=C(C=2)Cl)N1Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 7-Chloro-2H-1,4-benzoxazin |
|---|---|
| IUPAC Name | — |
| CAS Number | 27320-99-6 |
| Database ID | 11830086 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
7-Chloro-2H-1,4-benzoxazin (CAS 27320-99-6) 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 11830086
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-283ee1daa88542a092dab7b95f6b5425Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Using 7-chloro-4H-benzo[1,4]oxazin-3-one (2.3 g, 13.5 mmol) and borane-THF (40 mL of a 1M solution in THF, 40 mmol) in THF (40 mL) to yield the title compound as a cream solid (2.2 g, 96%). δH (CDCl3) 3.34-3.40 (2H, m), 4.16-4.28 (2H, m), 6.51-6.55 (1H, m), 6.59 (1H, d, J 2.4 Hz), 6.68 (1H, dd, J 8.1, 0.4 Hz). LCMS (ES+) 170 (M+H)+.
Source ID: ord-fb4857b93b88418da65f030b12f25cacConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-283ee1daa88542a092dab7b95f6b5425Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-283ee1daa88542a092dab7b95f6b5425Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 7-Chloro-4H-benzo[1,4]oxazin-3-one (81MF2271a) (1.74 g, 9.47 mmol), Cs2CO3 (4.63 g, 14.2 mmol) and 3-chloro-1-iodopropane (2.13 g, 10.4 mmol) were mixed according to GP6. CC (SiO2; Heptane/EtOAc 10:1-5) gave the title compound (81MF2271b) (1.95 g, 79%). 1H NMR (CDCl3) δ 7.03-6.96 (m, 3H), 4.59 (s, 2H), 4.07 (t, J=7.2 Hz, 2H), 3.61 (t, J=6.4 Hz, 2H), 2.17-2.10 (m, 2H); 13C NMR (CDCl3) δ 164.0, 146.0, 129.1, 127.3, 123.0, 117.8, 115.5, 67.7, 42.4, 39.2, 30.0.
Source ID: ord-4d9abbe0eec34f0d84ce51a0c72bdccdConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Using 7-chloro-4H-benzo[1,4]oxazin-3-one (2.3 g, 13.5 mmol) and borane-THF (40 mL of a 1M solution in THF, 40 mmol) in THF (40 mL) to yield the title compound as a cream solid (2.2 g, 96%). δH (CDCl3) 3.34-3.40 (2H, m), 4.16-4.28 (2H, m), 6.51-6.55 (1H, m), 6.59 (1H, d, J 2.4 Hz), 6.68 (1H, dd, J 8.1, 0.4 Hz). LCMS (ES+) 170 (M+H)+.
Source ID: ord-fb4857b93b88418da65f030b12f25cacConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 7-Chloro-4H-benzo[1,4]oxazin-3-one (81MF2271a) (1.74 g, 9.47 mmol), Cs2CO3 (4.63 g, 14.2 mmol) and 3-chloro-1-iodopropane (2.13 g, 10.4 mmol) were mixed according to GP6. CC (SiO2; Heptane/EtOAc 10:1-5) gave the title compound (81MF2271b) (1.95 g, 79%). 1H NMR (CDCl3) δ 7.03-6.96 (m, 3H), 4.59 (s, 2H), 4.07 (t, J=7.2 Hz, 2H), 3.61 (t, J=6.4 Hz, 2H), 2.17-2.10 (m, 2H); 13C NMR (CDCl3) δ 164.0, 146.0, 129.1, 127.3, 123.0, 117.8, 115.5, 67.7, 42.4, 39.2, 30.0.
Source ID: ord-032a4d6ef94d429eb6fd5770880b46b5Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 7-Chloro-4H-benzo[1,4]oxazin-3-one (81MF2271a) (1.74 g, 9.47 mmol), Cs2CO3 (4.63 g, 14.2 mmol) and 3-chloro-1-iodopropane (2.13 g, 10.4 mmol) were mixed according to GP6. CC (SiO2; Heptane/EtOAc 10:1-5) gave the title compound (81MF2271b) (1.95 g, 79%). 1H NMR (CDCl3) d 7.03-6.96 (m, 3H), 4.59 (s, 2H), 4.07 (t, J=7.2 Hz, 2H), 3.61 (t, J=6.4 Hz, 2H), 2.17-2.10 (m, 2H); 13C NMR (CDCl3) d 164.0, 146.0, 129.1, 127.3, 123.0, 117.8, 115.5, 67.7, 42.4, 39.2, 30.0.
Source ID: ord-584c1d21114b40e9aa59d82abc8d9a21Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 7-Chloro-4H-benzo[1,4]oxazin-3-one (81MF2271a) (1.74 g, 9.47 mmol), Cs2CO3 (4.63 g, 14.2 mmol) and 3-chloro-1-iodopropane (2.13 g, 10.4 mmol) were mixed according to GP6. CC (SiO2; Heptane/EtOAc 10:1-5) gave the title compound (81MF2271b) (1.95 g, 79%). 1H NMR (CDCl3) δ 7.03-6.96 (m, 3H), 4.59 (s, 2H), 4.07 (t, J=7.2 Hz, 2H), 3.61 (t, J=6.4 Hz, 2H), 2.17-2.10 (m, 2H); 13C NMR (CDCl3) δ 164.0, 146.0, 129.1, 127.3, 123.0, 117.8, 115.5, 67.7, 42.4, 39.2, 30.0.
Source ID: ord-4d9abbe0eec34f0d84ce51a0c72bdccdConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 7-Chloro-4H-benzo[1,4]oxazin-3-one (81MF2271a) (1.74 g, 9.47 mmol), Cs2CO3 (4.63 g, 14.2 mmol) and 3-chloro-1-iodopropane (2.13 g, 10.4 mmol) were mixed according to GP6. CC (SiO2; Heptane/EtOAc 10:1-5) gave the title compound (81MF2271b) (1.95 g, 79%). 1H NMR (CDCl3) δ 7.03-6.96 (m, 3H), 4.59 (s, 2H), 4.07 (t, J=7.2 Hz, 2H), 3.61 (t, J=6.4 Hz, 2H), 2.17-2.10 (m, 2H); 13C NMR (CDCl3) δ 164.0, 146.0, 129.1, 127.3, 123.0, 117.8, 115.5, 67.7, 42.4, 39.2, 30.0.
Source ID: ord-e5779b274f2b40d094d2fcecb21f8641Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 2-chloro-1-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-ethanone (1) (331 mg, 1.1 mmol, 1 equiv) in 5 ml of DMF, 4H-Benzo[1,4]oxazin-3-one (28) (200 mg, 1.1 mmol, 1.0 equiv) and cesium carbonate (710 mg, 2.2 mmol, 2 equiv) was stirred at RT overnight. The reaction solution was diluted with EtOAc, and the organic solution was washed with water. Purification of the crude reaction mixture using flash chromatography provided 7-chloro-4-{2-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-4H-benzo[1,4]oxazin-3-one (29): LCMS Retention time, 2.58 min.; LCMS observed (M+H)+: 450. the organic solution was washed with water Purification of the crude reaction mixture
Source ID: ord-f564eafd8bac4e5a8b59803d6ef64c51Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 2-amino-5-chloro-phenol (27) (2.0 g, 14 mmol, 1 equiv) in 30 ml of THF, chloroacetyl chloride (1.26 ml, 16.8 mmol, 1.2 equiv), and saturated aqueous NaHCO3 50 mL was stirred at RT for 2 hrs and then heated at 80° C. overnight. The reaction mixture was diluted with EtOAc, and washed with water. Purification of the crude product by flash chromatography provided 7-chloro-4H-benzo[1,4]oxazin-3-one (28): LCMS Retention time: 1.48 min.; LCMS observed (M+H)+: 184. heated at 80° C. overnight washed with water Purification of the crude product by flash chromatography
Source ID: ord-fe26fbf7e13e4c3c935a734864472926PubChem References
These sources are listed in the compound's public database record.
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