Water → HCID 19905431, compound

HRID 2371916Notes

Reaction equation

HRID 2371916 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[C:11]([C:13]1[N:14]([S:20](=[O:25])(=[O:24])[N:21]([CH3:23])[CH3:22])[CH:15]=[C:16]([CH2:18][OH:19])[N:17]=1)#[N:12].C(N(CC)CC)C.O>ClCCl>[C:11]([C:13]1[N:14]([S:20](=[O:24])(=[O:25])[N:21]([CH3:22])[CH3:23])[CH:15]=[C:16]([CH2:18][O:19][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:17]=1)#[N:12]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 199054352-Cyano-4-(hydroxymethyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide

Product 1

HCID 19905431HCID 19905431, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Chlorobenzoyl chloride (0.83 g) was added to a solution of 2-cyano-4-hydroxymethyl-1-(dimethylsulphamoyl)-imidazole (1.5 g) in dichloromethane (50 ml), containing triethylamine (1.0 ml) at 0°. The mixture was stirred for 45 minutes whilst the temperature was allowed to rise to room temperature. The mixture was added to water and the organic phase was separated, washed, dried and concentrated under reduced pressure. The residue was recrystallised from a mixture of diisopropyl ether and ethyl acetate to give 2-cyano-4-(4-chlorobenzoyloxy-methyl)-1-(dimethylsulphamoyl)imidazole, m.p. 94≥-96°. (Compound 1)

Workup

  1. customto rise to room temperature
  2. customthe organic phase was separated
  3. washwashed
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallised from a mixture of diisopropyl ether and ethyl acetate

Sources & evidence

ORD record
ord-609986e4b6354dc9a9729ca95b02c0cf
Source dataset
uspto-grants-1992_03
Patent number
US05096915

Reaction notes

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