Dimethylamine → HCID 54488087, compound

HRID 274610Notes

Reaction equation

HRID 274610 reaction equation
C(O[C@@:5]([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1[F:25])([C@H:12]([S:14](Cl)(=[O:16])=[O:15])[CH3:13])[CH2:6][N:7]1[CH:11]=[N:10][CH:9]=[N:8]1)(=O)C.[CH3:26][NH:27][CH3:28]>ClCCl>[CH3:26][N:27]([CH3:28])[S:14]([C:12](=[C:5]([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1[F:25])[CH2:6][N:7]1[CH:11]=[N:10][CH:9]=[N:8]1)[CH3:13])(=[O:15])=[O:16]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 10430695HCID 10430695, compound

Product 1

HCID 54488087HCID 54488087, compoundYield 18.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In dichloromethane (15 ml) was dissolved (2R,3R)-3-chlorosulfonyl-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butyl acetate (3.0 g). To the solution was added, under ice-cooling, dimethylamine (0.6 g). The reaction mixture was stirred for 10 minutes under ice-cooling, which was then concentrated. The concentrate was subjected to a silica gel chromatography (eluent: hexane/ethyl acetate=1/2→ethyl acetate) for purification to give, as the first eluate, N,N-dimethyl-3-(2,4-difluorophenyl)-4-(1H-1,2,4-triazol-1-yl)-2-butene-2-sulfonamide (isomer B, Compound 35, 0.48 g) as a pale yellow oily substance, and, as the second eluate, N,N-dimethyl-3-(2,4-difluorophenyl)-4-(1H-1,2,4-triazol-1-yl)-2-butene-2-sufonamide (isomer A, Compound 34, 0.80 g) as a pale yellow oily substance.

Workup

  1. additionTo the solution was added, under ice-
  2. temperaturecooling
  3. temperaturecooling
  4. concentrationwhich was then concentrated
  5. customThe concentrate was subjected to a silica gel chromatography (eluent: hexane/ethyl acetate=1/2→ethyl acetate) for purification

Sources & evidence

ORD record
ord-ebbc21daa3d948b2bd082ad6e4a73910
Source dataset
uspto-grants-1995_02
Patent number
US05389663

Reaction notes

Loading…