Acetic Anhydride → HCID 86600475, compound

HRID 851921Notes

Reaction equation

HRID 851921 reaction equation
[CH2:1]([O:8][NH:9][CH2:10][CH:11]1[C:16](=[O:17])[NH:15][C:14]2[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=2[S:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22](OC(=O)C)(=[O:24])C>C(O)=O.CCOC(C)=O>[CH2:1]([O:8][N:9]([CH2:10][CH:11]1[C:16](=[O:17])[NH:15][C:14]2[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=2[S:12]1)[CH:22]=[O:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 86600474HCID 86600474, compound

Product 1

HCID 86600475HCID 86600475, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(benzyloxyamino-methyl)-4H-benzo[1,4]thiazin-3-one (2.96 mmol) in 15 mL of formic acid at 0° C., acetic anhydride is added (15.1 mmol) and the reaction is stirred at room temperature overnight. The mixture is diluted with EtOAc and washed with water followed by brine and NaHCO3. Purification by column chromatography (hexane/EtOAc) gives N-benzyloxy-N-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-2-ylmethyl)-formamide. Yield: 81%. MS: (ES+): 329.2 [M+1].

Workup

  1. washwashed with water
  2. customPurification by column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-cbc9fd7bcfaa42338f4c62ef0b18bb14
Source dataset
uspto-grants-2007_08
Patent number
US07253164B2

Reaction notes

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