Water → 2-[N-(Tosyl)-N-(dimethylcarbamoylmethyl)amino]-5-chlorophenyl cyclohexyl ketone

HRID 374633Notes

Reaction equation

HRID 374633 reaction equation
[CH:1]1([C:7]([C:9]2[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=2[NH:16][S:17]([C:20]2[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=2)(=[O:19])=[O:18])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH3:29]C(C)(Br)C(N)=O.O.[CH3:37][N:38]([CH:40]=[O:41])[CH3:39]>>[CH:1]1([C:7]([C:9]2[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=2[N:16]([S:17]([C:20]2[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=2)(=[O:18])=[O:19])[CH2:29][C:40](=[O:41])[N:38]([CH3:39])[CH3:37])=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 1012352-Bromo-2-methylpropanamideHCID 537784895-Chloro-2-tosylaminophenyl cyclohexyl ketone

Product 1

HCID 543616542-[N-(Tosyl)-N-(dimethylcarbamoylmethyl)amino]-5-chlorophenyl cyclohexyl ketone

Procedure

4.3 g of 5-chloro-2-tosylaminophenyl cyclohexyl ketone are placed in 20 ml of DMF in the presence of 360 mg of 80% sodium hydride, after 15 minutes at RT 5.4 g of the compound prepared in step B are added and the mixture is stirred overnight at RT. The reaction medium is poured into water and the precipitate is filtered off and then taken up with DCM, dried and concentrated. The expected product crystallizes from isopropyl ether.

Workup

  1. filtrationthe precipitate is filtered off
  2. customdried
  3. concentrationconcentrated
  4. customThe expected product crystallizes from isopropyl ether

Sources & evidence

ORD record
ord-ad0f3b452332480fadc31a3f69dbfa9c
Source dataset
uspto-grants-1996_01
Patent number
US05481005

Reaction notes

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