Acetic Anhydride → HCID 67050629, compound

HRID 2385944Notes

Reaction equation

HRID 2385944 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[S:12][C:13]([C:15]([N:17]([C:19]4[CH:24]=[C:23]([C:25](=[O:30])[NH:26][CH2:27][CH2:28][OH:29])[CH:22]=[CH:21][C:20]=4[Cl:31])[CH3:18])=[O:16])=[CH:14][C:10]=3[CH2:9][CH2:8][O:7][C:6]=2[CH:32]=1.[C:33](OC(=O)C)(=[O:35])[CH3:34]>N1C=CC=CC=1>[C:33]([O:29][CH2:28][CH2:27][NH:26][C:25](=[O:30])[C:23]1[CH:22]=[CH:21][C:20]([Cl:31])=[C:19]([N:17]([CH3:18])[C:15]([C:13]2[S:12][C:11]3[C:5]4[CH:4]=[CH:3][C:2]([Br:1])=[CH:32][C:6]=4[O:7][CH2:8][CH2:9][C:10]=3[CH:14]=2)=[O:16])[CH:24]=1)(=[O:35])[CH3:34]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 67050562HCID 67050562, compound

Product 1

HCID 67050629HCID 67050629, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

8-Bromo-N-(2-chloro-5-(2-hydroxyethylcarbamoyl)phenyl)-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide (0.5 g, 0.933 mmol) was dissolved in 5 mL of pyridine. The mixture was stirred at 0° C. and acetic anhydride (0.2 g, 2 eq) was added dropwise. It was stirred at room temperature for overnight. The mixture was poured into ice water and the mixture was extracted by DCM. The combined organics were dried and evaporated in vacuum to afford the acetylated product, 2-(3-(8-bromo-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamido)-4-chlorobenzamido)ethyl acetate (0.45 g, yield: 83%). LC-MS: (ESI, m/z)=577 [M+H]+

Workup

  1. stirringIt was stirred at room temperature for overnight
  2. extractionthe mixture was extracted by DCM
  3. customThe combined organics were dried
  4. customevaporated in vacuum

Sources & evidence

ORD record
ord-08590cf9db6f41819eaae96c1c5bd72e
Source dataset
uspto-grants-2012_09
Patent number
US08263633B2

Reaction notes

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