Thiourea → HCID 178451223, 화합물

HRID 2389463노트

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HRID 2389463 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

HCID 178451223HCID 178451223, 화합물수율 92.9%

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-aacda600cbb84607942fb46c6aa58064
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08273740B2

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