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

HRID 231160Notes

Reaction equation

HRID 231160 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.Cl[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21]>>[CH2:23]([O:22][C:20]([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:21])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 10387Benzyl chloroformateHCID 139233692-(4-Methoxy-2-picolylmercapto)-1H-thieno[3,4-d]imidazole

Product 1

HCID 200346151-Benzyloxycarbonyl-2-(4-methoxy-2-picolylmercapto)-1H-thieno[3,4-d]imidazoleYield 106.9%

Procedure

1.4 g (5 mmol) of 2-(4-methoxy-2-picolylmercapto)-1H-thieno[3,4-d]imidazole were reacted in analogy to Example 15 with 0.8 ml (5 mmol) of benzyl chloroformate (90-95%). 2.2 g of oily crude product were obtained and were chromatographed on silica gel (35-70μ) with toluene/ethyl acetate (1:5). The product crystallized from diethyl ether. Melting point 102°-104° C.

Sources & evidence

ORD record
ord-c1ffb5bcc8da4f6a8a20866adaa62f93
Source dataset
uspto-grants-1989_07
Patent number
US04845118

Reaction notes

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