1,1'-Thiocarbonyldiimidazole → HCID 178506355, compound

HRID 1696679

Reaction equation

HRID 1696679 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[S:2].[F:13][C:14]([F:25])([F:24])[O:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[C:18]([NH2:23])[CH:17]=1>O1CCCC1>[SH:2][C:1]1[NH:23][C:18]2[CH:17]=[C:16]([O:15][C:14]([F:24])([F:25])[F:13])[CH:21]=[CH:20][C:19]=2[N:22]=1

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 27739594-(Trifluoromethoxy)benzene-1,2-diamine

Product 1

HCID 178506355HCID 178506355, compoundYield 103.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,1′-thiocarbonyldiimidazole (1.13 g, 6.25 mmol) is added by portions to a solution of 4-(trifluoromethoxy)-ortho-phenylenediamine (1 g, 5.2 mmol) in 5 ml of tetrahydrofuran and the mixture 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. The residue is triturated in diisopropylether and pentane and dried under vacuum to yield 1.26 g of 2-mercapto-5-trifluoromethoxy-benzimidazole as a yellow powder. Quantitative yield. Analytical LC/MS (method B): retention time=3.69 min. m/z=235.67 (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
  7. customThe residue is triturated in diisopropylether
  8. dry with materialpentane and dried under vacuum

Sources & evidence

ORD record
ord-b2377a823b6743a491300075ff1f4a6b
Source dataset
uspto-grants-2012_04
Patent number
US08163768B2

Linked notes

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