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

HRID 1608847Notes

Reaction equation

HRID 1608847 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 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-309adad56829427f9d0ebc7ba0ad811a
Source dataset
uspto-grants-1995_03
Patent number
US05397801

Reaction notes

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