Acetic Anhydride → HCID 70591618, compound

HRID 1732927Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:10]([C:14]([OH:16])=[O:15])=[CH:11][S:12][CH:13]=2)[CH:5]=[CH:4][C:3]=1[CH3:17].[C:18](OC(=O)C)(=[O:20])[CH3:19]>>[C:18]([NH:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:10]([C:14]([OH:16])=[O:15])=[CH:11][S:12][CH:13]=2)[CH:5]=[CH:4][C:3]=1[CH3:17])(=[O:20])[CH3:19]

Participants

Reactant 2

HCID 7918Acetic Anhydride

HCID 70590282HCID 70590282, compound

Product 1

HCID 70591618HCID 70591618, compound

Procedure

When 7-methyl-thieno[3,4-b][1,5]benzoxazepin-10-(9H)-one is refluxed for 16 hours in 5 N sodium hydroxide, diluted with water, adjusted to pH 4-5 with dilute hydrochloric acid and extracted with methylene chloride, 4-(2-amino-p-tolyloxy)-3-thiophenecarboxylic acid (IX) is obtained. Compound IX is treated with acetic anhydride and extracted with ether to give 4-(2-acetamido-p-tolyloxy)-3-thiophenecarboxylic acid (X). When a stirred mixture of X and lithium aluminum hydride in ether is refluxed for 16 hours and the resulting product is dissolved in ether and treated with alcoholic hydrochloric acid, the compound 4-(2-ethylamino-p-tolyloxy)-3-thiophenemethanol hydrochloride (XI) is obtained.

Workup

extractionextracted with ether

Sources & evidence

ORD record: ord-e0c5763f493f4b92aa18d0dd410bf736
Source dataset: uspto-grants-1980_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04239898

Reaction notes

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