Thiourea → HCID 178451223, compound

HRID 2389463Notes

Reaction equation

HRID 2389463 reaction equation
Cl[C:2]1[N:6]([CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=2[N:3]=1.NC(N)=[S:21]>CO>[C:11]([O:10][C:8](=[O:9])[CH2:7][N:6]1[C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=2[N:3]=[C:2]1[SH:21])([CH3:14])([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 86224963tert-Butyl (2-chloro-benzoimidazol-1-yl)-acetate

Product 1

HCID 178451223HCID 178451223, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

According to the procedure described in: Migawa, M. T.; Girardet, J.-L.; Walker II, J. A.; Koszalka, G. W.; Chamberlain, S. D.; Drach, J. C.; Townsend, L. B., J. Med. Chem. 1998, 41, 1242-1251, a solution of tert-butyl (2-chloro-benzoimidazol-1-yl)-acetate (Intermediate 2-I, 7 g, 26.3 mmol) and thiourea (7.98 g, 105 mmol) in methanol (100 ml) is refluxed for 2 h. The mixture is cooled down and most of the methanol is removed in vacuo. After addition of saturated aqueous NH4Cl solution (150 ml), the resulting aqueous phase is extracted three times with Et2O. The combined organic phases are washed with brine and dried over Na2SO4. The solvent is evaporated in vacuo and the residue dried under high vacuum, yielding the title compound (6.46 g) in 93% as a white powder: tR=6.14 min (LC-1), ESI-MS (neg.): m/z 263.31 [M−H]+; 1H-NMR (CDCl3): δ (ppm) 1.50 (s, 9H, tBu), 4.94 (s, 2H, CH2CO2), 6.99-7.05 (m, 1 Harom), 7.16-7.24 (m, 1Harom), 10.69 (bs, 1H, SH).

Workup

  1. customis removed in vacuo
  2. additionAfter addition of saturated aqueous NH4Cl solution (150 ml)
  3. extractionthe resulting aqueous phase is extracted three times with Et2O
  4. washThe combined organic phases are washed with brine
  5. dry with materialdried over Na2SO4
  6. customThe solvent is evaporated in vacuo
  7. customthe residue dried under high vacuum

Sources & evidence

ORD record
ord-aacda600cbb84607942fb46c6aa58064
Source dataset
uspto-grants-2012_09
Patent number
US08273740B2

Reaction notes

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