Hydrogen Sulfide → HCID 22819082, compound

HRID 1447008Notes

Reaction equation

HRID 1447008 reaction equation
[C:1]([C:3]1[N:4]=[CH:5][N:6]([C@@H:11]2[O:31][C@H:30]([CH2:32][O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C@@H:21]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C@@H:12]2[O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:7]=1[CH2:8][C:9]#[N:10])#[N:2].C(O)C.[SH2:44]>C(N(CC)CC)C>[NH2:10][C:9]1[NH:2][C:1](=[S:44])[C:3]2[N:4]=[CH:5][N:6]([C@@H:11]3[O:31][C@H:30]([CH2:32][O:33][CH2:34][C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)[C@@H:21]([O:22][CH2:23][C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[C@@H:12]3[O:13][CH2:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:7]=2[CH:8]=1

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 702EthanolHCID 54238159HCID 54238159, compound

Product 1

HCID 22819082HCID 22819082, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 8 g of 4-cyano-5-cyanomethyl-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)imidazole, 250 ml of ethanol saturated at 0° C. with hydrogen sulfide, and 2.5 g of triethylamine is kept in a steel bomb for 48 hours at ambient temperature. The reaction solution is evaporated in vacuo to a yellow foam which is coevaporated with ethanol several times to provide 6-amino-1,5-dihydro-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-4H-imidazo[4,5-c]pyridine-4-thione.

Workup

  1. customThe reaction solution is evaporated in vacuo to a yellow foam which

Sources & evidence

ORD record
ord-44fc597d4e9e4a3d8c9d383edd0eeb3a
Source dataset
uspto-grants-1982_02
Patent number
US04315000

Reaction notes

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