Water → HCID 19754602, compound

HRID 1588796Notes

Reaction equation

HRID 1588796 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:17]([NH2:18])=[CH:16][N:15]=[CH:14]1.[F:19][C:20]([F:24])([F:23])[S:21]Cl.O>C(Cl)Cl>[Cl:12][C:4]1[CH:5]=[C:6]([C:8]([F:10])([F:11])[F:9])[CH:7]=[C:2]([Cl:1])[C:3]=1[N:13]1[C:17]([NH2:18])=[C:16]([S:21][C:20]([F:24])([F:23])[F:19])[N:15]=[CH:14]1

Participants

5

Reactant 3

HCID 962WaterHCID 67900Methanesulfenyl chloride, trifluoro-HCID 19754555HCID 19754555, compound

Product 1

HCID 19754602HCID 19754602, compoundYield 56.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4.8 g (14.91 mmole) of 1-(2,6-dichloro-4-trifluoromethylphenyl)-5-aminoimidazole in 400 ml of methylene chloride was added 1.3 ml (14.91 mmole) of trifluoromethanesulfenyl chloride at 0° C. The mixture was stirred at 0° C. for 4 h and then at RT for 15 h. Water was added and the mixture was partitioned between water and methylene chloride. The organic layer was dried over anhydrous sodium sulfate and the solvent removed. The residue was recrystallized from methylene chloride to give 3.36 g (52.51% yield) of the desired product., mp 134° C.

Workup

  1. waitat RT for 15 h
  2. customthe mixture was partitioned between water and methylene chloride
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent removed
  5. customThe residue was recrystallized from methylene chloride

Sources & evidence

ORD record
ord-29ff528fcd0f4e03b8ba1157d964ed9d
Source dataset
uspto-grants-1993_06
Patent number
US05223525

Reaction notes

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