Sodium hydride → 8-(6-Methyl-2-oxo-benzoxazolin-3-yl)-caprylic acid methyl ester

HRID 355035Notes

Reaction equation

HRID 355035 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:13]=[CH:12][C:7]2[NH:8][C:9](=[O:11])[O:10][C:6]=2[CH:5]=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:8]1[C:7]2[CH:12]=[CH:13][C:4]([CH3:3])=[CH:5][C:6]=2[O:10][C:9]1=[O:11]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 3226346-methyl-1,3-benzoxazol-2(3H)-oneHCID 11107373Methyl 8-bromooctanoate

Product 1

HCID 541327788-(6-Methyl-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 3.6 g. of NaH (of 80% suspension in mineral oil), 19.9 g. of 6-methylbenzoxazolin-2-one (produced in usual manners by subjecting 2-amino-5-methyl-phenol-hydrochloride to reaction with phosgene), 240 cc. of DMF, 28.4 g. of 8-bromo caprylic acid methyl ester and 3.6 g. NaJ.

Workup

  1. customThe product is produced

Sources & evidence

ORD record
ord-5deb0d187efb4ec6b279fee92c0f5b74
Source dataset
uspto-grants-1983_03
Patent number
US04377695

Reaction notes

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