Ammonia → HCID 54275155, compound

HRID 274611Notes

Reaction equation

HRID 274611 reaction equation
ClCCl.C(O[C@@:8]([C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=1[F:28])([C@H:15]([S:17](Cl)(=[O:19])=[O:18])[CH3:16])[CH2:9][N:10]1[CH:14]=[N:13][CH:12]=[N:11]1)(=O)C.[NH3:29]>C(OCC)(=O)C>[F:28][C:22]1[CH:23]=[C:24]([F:27])[CH:25]=[CH:26][C:21]=1[C:8]([CH2:9][N:10]1[CH:14]=[N:13][CH:12]=[N:11]1)=[C:15]([S:17]([NH2:29])(=[O:19])=[O:18])[CH3:16]

Participants

5

Reactant 3

HCID 222Ammonia2×HCID 6344DichloromethaneHCID 10430695HCID 10430695, compound

Product 1

HCID 54275155HCID 54275155, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A dichloromethane (30 ml) solution of (2R,3R)-3-chlorosulfonyl-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butyl acetate (2.0 g) was cooled to -30° C., to which was introduced ammonia for 10 minutes. To the mixture was introduced nitrogen to eliminate ammonia. To the reaction mixture was added ethyl acetate (50 ml), then precipitating crystals were collected by filtration, followed by recrystallization from methanol to give 3-(2,4-difluorophenyl)-4-(1H-1,2,4-triazol-1-yl)-2-butene-2-sulfonamide (isomer A, Compound 36, 0.54 g) as colorless crystals.

Workup

  1. additionTo the mixture was introduced nitrogen
  2. customprecipitating crystals
  3. filtrationwere collected by filtration
  4. customfollowed by recrystallization from methanol

Sources & evidence

ORD record
ord-342f9b3b2aab4b1c989c834795d33f42
Source dataset
uspto-grants-1995_02
Patent number
US05389663

Reaction notes

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