Ethyl chloroformate → 1-Ethoxycarbonyl-2-(4-methoxy-2-picolylmercapto)-1H-thieno[3,4-d]imidazole

HRID 231157Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][S:10][C:11]2[NH:15][C:14]3=[CH:16][S:17][CH:18]=[C:13]3[N:12]=2)[CH:4]=1.[H-].[Na+].Cl[C:22]([O:24][CH2:25][CH3:26])=[O:23]>CN(C)C=O>[CH2:25]([O:24][C:22]([N:12]1[C:13]2=[CH:18][S:17][CH:16]=[C:14]2[N:15]=[C:11]1[S:10][CH2:9][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][N:6]=1)=[O:23])[CH3:26]

Participants

Conditions

Temperature: 36 °C

Procedure

Under nitrogen, 1.4 g (5.0 mmol) of 2-(4-methoxy-2-picolylmercapto)-1H-thieno[3,4-d]imidazole were dissolved in 15 ml of anhydrous dimethylformamide, and 270 mg (6 mmol) of a 60% suspension of NaH in oil were added in portions, and the mixture was heated at 30°-40° C. for 10 minutes. Now, at 25° C., 0.5 ml (5 mmol) of ethyl chloroformate (95%) was added, during which the temperature increases to about 36° C. 30 minutes later the crystalline product was filtered off with suction and washed twice with diethyl ether. Melting point 154°-156° C. (decomposition).

Workup

temperaturethe mixture was heated at 30°-40° C. for 10 minutes
filtration30 minutes later the crystalline product was filtered off with suction
washwashed twice with diethyl ether

Sources & evidence

ORD record: ord-166da5729a2d429da3f5e4c390a06e81
Source dataset: uspto-grants-1989_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04845118

Reaction notes

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