Thiourea → HCID 86625962, compound

HRID 418559Notes

Reaction equation

HRID 418559 reaction equation
O1[CH2:3][CH:2]1[CH:4]([CH3:27])[CH2:5][S:6]([C:9]1[CH:26]=[CH:25][C:12]([O:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:16][CH:15]=2)=[CH:11][CH:10]=1)(=[O:8])=[O:7].NC(N)=[S:30]>CO.C(Cl)Cl>[S:30]1[CH2:3][CH:2]1[CH:4]([CH3:27])[CH2:5][S:6]([C:9]1[CH:26]=[CH:25][C:12]([O:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:16][CH:15]=2)=[CH:11][CH:10]=1)(=[O:8])=[O:7]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 86625963HCID 86625963, compound

Product 1

HCID 86625962HCID 86625962, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a stirred solution of 1.9 (500 mg, 1.38 mmol) in MeOH—CH2Cl2 (10:1, 11 mL) was added thiourea (262 mg, 3.45 mmol) at room temperature, and the mixture was stirred overnight. After concentration under reduced pressure, the residue was dissolved in ethyl ether. The ethyl ether solution was washed with water and brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=2/5) to give 1.3 (400 mg, 77%) as a colorless oil. 1H NMR (500 MHz, CDCl3): δ 2.15 (dd, 1H, J=5.5, 2.0 Hz), 2.53 (dd, 1H, J=6.5, 2.0 Hz), 3.05 (m, 1H), 3.17 (dd, 1H, J=14.5, 7.0 Hz), 3.51 (dd, 1H, J=14.5, 5.5 Hz), 3.65 (s, 2H), 3.72 (s, 3H), 7.03-7.05 (m, 2H), 7.08-7.10 (m, 2H), 7.33-7.34 (m, 2H), 7.85-7.86 (m, 2H); 13C NMR (125 MHz, CDCl3): δ 24.2, 26.0, 40.3, 52.1, 62.6, 117.7, 120.5, 130.7, 130.9, 131.1, 131.9, 153.8, 162.8, 171.8; HRMS (FAB) calcd for C18H19O5S2 (M+H+) 379.0674. found 379.0645.

Workup

  1. concentrationAfter concentration under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl ether
  3. washThe ethyl ether solution was washed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=2/5)

Sources & evidence

ORD record
ord-ab1ace5e95b4400e8a7b0a769e7bd33d
Source dataset
uspto-grants-2012_01
Patent number
US08093287B2

Reaction notes

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