Water → tert-Butyl [4-(1H-benzimidazol-2-yl)-1,3-thiazol-2-yl]methyl-carbamate

HRID 2213151

Reaction equation

HRID 2213151 reaction equation
O(C)[Na].[C:4]([C:6]1[N:7]=[C:8]([CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[S:9][CH:10]=1)#[N:5].Cl.Cl.[C:22]1(N)[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[NH2:28].O>CO>[NH:5]1[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[N:28]=[C:4]1[C:6]1[N:7]=[C:8]([CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:18])[CH3:17])[S:9][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 119901,2-Phenylenediamine dihydrochlorideHCID 22560011Tert-butyl ((4-cyanothiazol-2-YL)methyl)carbamateHCID 178418582HCID 178418582, compound

Product 1

HCID 86760240tert-Butyl [4-(1H-benzimidazol-2-yl)-1,3-thiazol-2-yl]methyl-carbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In analogy to the preparation of 8, 1.89 g of a 30% NaOCH3 solution were added to tert-butyl (4-cyano-1,3-thiazol-2-yl)methylcarbamate (2.5 g; 10.45 mmol) in 25 ml of CH3OH, and the mixture was stirred at room temperature for 2 h. Addition of 1.9 g of 1,2-phenylenediamine bishydrochloride was followed by stirring overnight, and then the reaction mixture was added to 100 ml of H2O, and the solid resulting after filtration was dried in vacuo.

Workup

  1. stirringby stirring overnight
  2. customthe solid resulting
  3. filtrationafter filtration
  4. customwas dried in vacuo

Sources & evidence

ORD record
ord-f5ebaded0d65491ca59edccccd7fba4b
Source dataset
uspto-grants-2006_09
Patent number
US07105508B1

Linked notes

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