1,1'-Thiocarbonyldiimidazole → HCID 178455021, compound

HRID 1696618Notes

Reaction equation

HRID 1696618 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[S:2].[C:13]([Si:17]([CH3:28])([CH3:27])[O:18][C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[C:21]([NH2:26])[CH:20]=1)([CH3:16])([CH3:15])[CH3:14]>O1CCCC1>[SH:2][C:1]1[NH:26][C:21]2[CH:20]=[C:19]([O:18][Si:17]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:28])[CH3:27])[CH:24]=[CH:23][C:22]=2[N:25]=1

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 672786584-((tert-Butyldimethylsilyl)oxy)benzene-1,2-diamine

Product 1

HCID 178455021HCID 178455021, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,1′-Thiocarbonyldiimidazole (1.87 g, 10.5 mmol) is added by portions to a solution of 4-(tert-butyl-dimethyl-silanyloxy)-ortho-phenylenediamine (2.5 g, 10.5 mmol) in 25 ml of tetrahydrofuran and the mixture is stirred at room temperature for 16 hours. The reaction mixture is then concentrated under reduced pressure, dissolved in 300 ml of ethyl acetate and washed with water (2×100 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 2.07 g of 2-mercapto-5-(tert-butyl-dimethyl-silanyloxy)-benzimidazole. Yield=70%. Analytical LC/MS (method B): retention time=4.79 min. m/z=281.36 (positive ion mode).

Workup

  1. concentrationThe reaction mixture is then concentrated under reduced pressure
  2. dissolutiondissolved in 300 ml of ethyl acetate
  3. washwashed with water (2×100 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-3cf862c53c2c4cf7bf839a79b0a45fc4
Source dataset
uspto-grants-2012_04
Patent number
US08163768B2

Reaction notes

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