Acetic Anhydride → n-[3-Acetylamino-4-(2-diethylamino-ethoxy)-phenyl]-2-(2-chloro-4-trifluoromethyl-phenoxy)-acetamide

HRID 898606Notes

Reaction equation

HRID 898606 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:16][C:17](=[O:31])[CH2:18][O:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][C:21]=2[Cl:30])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][N:11]([CH2:14][CH3:15])[CH2:12][CH3:13].[C:32](OC(=O)C)(=[O:34])[CH3:33]>>[C:32]([NH:1][C:2]1[CH:3]=[C:4]([NH:16][C:17](=[O:31])[CH2:18][O:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:27])([F:28])[F:29])=[CH:22][C:21]=2[Cl:30])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][N:11]([CH2:12][CH3:13])[CH2:14][CH3:15])(=[O:34])[CH3:33]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 59691580n-[3-Amino-4-(2-diethylamino-ethoxy)-phenyl]-2-(2-chloro-4-trifluoromethyl-phenoxy)-acetamide

Product 1

HCID 59691673n-[3-Acetylamino-4-(2-diethylamino-ethoxy)-phenyl]-2-(2-chloro-4-trifluoromethyl-phenoxy)-acetamide

Procedure

A solution of 100 mg (0.217 mmol) N-[3-amino-4-(2-diethylamino-ethoxy)-phenyl]-2-(2-chloro-4-trifluoromethyl-phenoxy)-acetamide (Example 160) in 10 mL acetic anhydride was stirred for 3 h at 100° C. and then evaporated down i. vac. The residue was combined with saturated aqueous sodium bicarbonate and exhaustively extracted with EtOAc. The combined org. phases were dried over sodium sulphate, evaporated down i. vac. and the residue was stirred with ether. The precipitate was filtered off, washed with ether and dried in a HV.

Workup

  1. customevaporated down i
  2. extractionexhaustively extracted with EtOAc
  3. dry with materialphases were dried over sodium sulphate
  4. customevaporated down i
  5. filtrationThe precipitate was filtered off
  6. washwashed with ether
  7. customdried in a HV

Sources & evidence

ORD record
ord-c7085788c7fc43a89b6e7c2a5fc0e730
Source dataset
uspto-grants-2008_04
Patent number
US07351719B2

Reaction notes

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