Water → HCID 21314981, compound

HRID 236997Notes

Reaction equation

HRID 236997 reaction equation
[F: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.C(NC(C)C)(C)C.[F:26][C:27]([F:31])=[C:28]([F:30])[F:29].O>CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([S:18][C:28]([F:30])([F:29])[CH:27]([F:31])[F:26])[NH:11][C:12]=2[C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7912DiisopropylamineHCID 8301TetrafluoroethyleneHCID 178505564HCID 178505564, compound

Product 1

HCID 21314981HCID 21314981, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 14.0 g of 4-(4-fluorophenyl)-5-(2-thienyl)-1H-2-imidazolethiol in 40 ml of dimethylformamide and 1.5 g of diisopropylamine was pressured in a bomb with 4 g of tetrafluoroethylene. The pressure dropped from 160 psi to 0 in 1.5 hrs. The solution was poured into water, stirred until most of gum solidified, filtered and washed with water. The solid was dissolved in chloroform, dried over anhydrous sodium sulfate, concentrated and diluted with 1-chlorobutane. The crystalline product was collected; yield 2.5 g, m.p. 164°-168° C. The residue from the filtrate was chromatographed on silica gel (Silicar CC-4) using chloroform to give 4.1 g, m.p. 167.5°-170° C. The combined 6.5 g was crystallized from 1-chlorobutane to give 5.6 g, m.p. 167°-168.5° C.

Workup

  1. additionThe pressure dropped from 160 psi to 0 in 1.5 hrs
  2. filtrationfiltered
  3. washwashed with water
  4. dissolutionThe solid was dissolved in chloroform
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. additiondiluted with 1-chlorobutane
  8. customThe crystalline product was collected
  9. customThe residue from the filtrate was chromatographed on silica gel (Silicar CC-4)
  10. customto give 4.1 g, m.p. 167.5°-170° C
  11. customThe combined 6.5 g was crystallized from 1-chlorobutane
  12. customto give 5.6 g, m.p. 167°-168.5° C.

Sources & evidence

ORD record
ord-ff8b8144d1cf42f9bf09464eaa1afe90
Source dataset
uspto-grants-1979_06
Patent number
US04159338

Reaction notes

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