1,1'-Thiocarbonyldiimidazole → HCID 178505912, compound

HRID 1696669Notes

Reaction equation

HRID 1696669 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[NH2:10].[C:11](N1C=CN=C1)(N1C=CN=C1)=[S:12]>O1CCCC1>[SH:12][C:11]1[NH:10][C:3]2[C:4]([F:9])=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[N:1]=1

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 27367541,2-Diamino-3,5-difluorobenzene

Product 1

HCID 178505912HCID 178505912, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1,2-diamino-3,5-difluorobenzene (1 g, 6.94 mmol) and 1,1′-thiocarbonyldiimidazole (2.05 g, 11.52 mmol) in 10 ml of tetrahydrofuran is stirred at room temperature for 16 hours. The reaction mixture is then concentrated under reduced pressure and the residue is dissolved in 100 ml of ethyl acetate and washed with water (2×30 ml). The organic phase is then dried over MgSO4, filtered and concentrated under reduced pressure to yield 763 mg of 2-mercapto-4,6-difluorobenzimidazole. Yield=61%. Analytical LC/MS (method B): retention time=2.49 min. m/z=186.95 (positive ion mode).

Workup

  1. concentrationThe reaction mixture is then concentrated under reduced pressure
  2. dissolutionthe residue is dissolved in 100 ml of ethyl acetate
  3. washwashed with water (2×30 ml)
  4. dry with materialThe organic phase is then dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9440f9e4154b4a29b781d804f690582f
Source dataset
uspto-grants-2012_04
Patent number
US08163768B2

Reaction notes

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