Water → HCID 21314995, compound

HRID 237001Notes

Reaction equation

HRID 237001 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([SH:18])[NH:11][C:12]=2[C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)=[CH:4][CH:3]=1.[F:19][C:20]([F:24])=[C:21]([F:23])[F:22].O>CN(C)C=O.C(NC(C)C)(C)C.ClCCCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([S:18][C:21]([F:23])([F:22])[CH:20]([F:24])[F:19])[NH:11][C:12]=2[C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 962WaterHCID 8301TetrafluoroethyleneHCID 178527836HCID 178527836, compound

Product 1

HCID 21314995HCID 21314995, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 7912DiisopropylamineSolventHCID 8005Butyl ChlorideSolvent

Procedure

A solution of 6.9 g of 4-(4-chlorophenyl)-5-(2-thienyl)-1H-2-imidazolethiol in 40 ml of dimethylformamide and 1.5 ml of diisopropylamine was pressured in a bomb with 3 g of tetrafluoroethylene and shaken until there was no further pressure drop. The bomb contents were poured into water, the pH adjusted to 8 and the solution extracted with chloroform. The extract was dried and concentrated. It was chromatographed on silica gel (Silicar CC-4) to give 5.5 g of a cut which was dissolved in hot 1-chlorobutane. On cooling 4.5 g of product was obtained, m.p. 161.5°-163° C.

Workup

  1. extractionthe solution extracted with chloroform
  2. customThe extract was dried
  3. concentrationconcentrated
  4. customIt was chromatographed on silica gel (Silicar CC-4)
  5. customto give 5.5 g of a cut which
  6. customwas obtained

Sources & evidence

ORD record
ord-09acd5ebf5c742e09a29a5976bd57e20
Source dataset
uspto-grants-1979_06
Patent number
US04159338

Reaction notes

Loading…