Chlorzoxazone → 8-(5-Chloro-2-oxo-benzoxazolin-3-yl)-caprylic acid methyl ester

HRID 355036Notes

Reaction equation

HRID 355036 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10](=[O:12])[NH:9][C:8]=2[CH:13]=1.[CH3:14][O:15][C:16](=[O:25])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]Br>CN(C=O)C>[CH3:14][O:15][C:16](=[O:25])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][N:9]1[C:8]2[CH:13]=[C:4]([Cl:3])[CH:5]=[CH:6][C:7]=2[O:11][C:10]1=[O:12]

Participants

5

Reactant 3

HCID 2733ChlorzoxazoneHCID 24758Sodium hydrideHCID 11107373Methyl 8-bromooctanoate

Product 1

HCID 129611658-(5-Chloro-2-oxo-benzoxazolin-3-yl)-caprylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product is produced as described in example 1 from 3 g. of NaH (80% suspension in mineral oil), 17 g. of 5-chloro-benzoxazolin-2-one (produced in usual manners by subjecting 2-amino-4-chloro-phenol-hydrochloride to reaction with phosgene), 200 cc. of DMF, 23.7 g. of 8-bromo-caprylic acid methyl ester and 3 g. of NaJ.

Workup

  1. customThe product is produced

Sources & evidence

ORD record
ord-1276cb9699e947f78b4dcbe8f2f4cf38
Source dataset
uspto-grants-1983_03
Patent number
US04377695

Reaction notes

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