Colchicine → Thiocholchicine

HRID 2052775Notes

Reaction equation

HRID 2052775 reaction equation
[CH3:1][C:2]([NH:4][C@@H:5]1[C:21]2[C:14](=[CH:15][CH:16]=[C:17](OC)[C:18]([CH:20]=2)=[O:19])[C:13]2[C:12]([O:24][CH3:25])=[C:11]([O:26][CH3:27])[C:10]([O:28][CH3:29])=[CH:9][C:8]=2[CH2:7][CH2:6]1)=[O:3].[CH3:30][S-:31].[Na+]>O>[CH3:1][C:2]([NH:4][C@@H:5]1[C:21]2[C:14](=[CH:15][CH:16]=[C:17]([S:31][CH3:30])[C:18]([CH:20]=2)=[O:19])[C:13]2[C:8](=[CH:9][C:10]([O:28][CH3:29])=[C:11]([O:26][CH3:27])[C:12]=2[O:24][CH3:25])[CH2:7][CH2:6]1)=[O:3]

Participants

4

Reactant 2

HCID 6167ColchicineHCID 4378561Sodium methanethiolate

Product 1

HCID 17648Thiocholchicine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Colchicine (1.25 mmole) was dissolved in 10.0 mL of water to which was added sodium methanethiolate (7.13 mmol). The yellow solution was stirred for 24 hours, then extracted 3× with ETOH:Chloroform (1:1), then evaporated to yield the desired compound as yellow crystals.

Workup

  1. extractionextracted 3× with ETOH
  2. customChloroform (1:1), then evaporated

Sources & evidence

ORD record
ord-9847e97939a745d88de102c31d00ce24
Source dataset
uspto-grants-2008_02
Patent number
US07326685B2

Reaction notes

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