Methanesulfonyl chloride → 2-(2-Chloro-4-trifluoromethyl-phenoxy)-n-[4-(2-diethylamino-ethoxy)-3-methanesulphonylamino-phenyl]-acetamide

HRID 898607Notes

Reaction equation

HRID 898607 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].[CH3:32][S:33](Cl)(=[O:35])=[O:34]>N1C=CC=CC=1>[Cl:30][C:21]1[CH:22]=[C:23]([C:26]([F:27])([F:28])[F:29])[CH:24]=[CH:25][C:20]=1[O:19][CH2:18][C:17]([NH:16][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:9][CH2:10][N:11]([CH2:12][CH3:13])[CH2:14][CH3:15])=[C:2]([NH:1][S:33]([CH3:32])(=[O:35])=[O:34])[CH:3]=1)=[O:31]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 59691580n-[3-Amino-4-(2-diethylamino-ethoxy)-phenyl]-2-(2-chloro-4-trifluoromethyl-phenoxy)-acetamide

Product 1

HCID 596917142-(2-Chloro-4-trifluoromethyl-phenoxy)-n-[4-(2-diethylamino-ethoxy)-3-methanesulphonylamino-phenyl]-acetamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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 5 mL pyridine was added at 0° C. to 18 μL (0.239 mmol) of methanesulphonylchloride, the mixture was slowly heated to RT and stirred for 3 h at RT. The reaction mixture was poured onto ice water and the aqueous phase was exhaustively extracted with EtOAc. The combined org. phases were dried over sodium sulphate and evaporated down i. vac. The residue was lyophilised.

Workup

  1. additionThe reaction mixture was poured onto ice water
  2. extractionthe aqueous phase was exhaustively extracted with EtOAc
  3. dry with materialphases were dried over sodium sulphate
  4. customevaporated down i

Sources & evidence

ORD record
ord-f182ad9747174478b076bb85a6791040
Source dataset
uspto-grants-2008_04
Patent number
US07351719B2

Reaction notes

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