Chloroform → HCID 19972905, compound

HRID 1451926Notes

Reaction equation

HRID 1451926 reaction equation
[CH3:1][NH:2][C:3]([C:5]1([N:12]2[CH:16]=[C:15]([CH3:17])[N:14]=[CH:13]2)[CH2:10][CH2:9][CH2:8][CH2:7][C:6]1=[O:11])=[S:4].[BH4-].[Na+].C(Cl)(Cl)Cl>CO>[OH:11][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][C:5]1([N:12]1[CH:16]=[C:15]([CH3:17])[N:14]=[CH:13]1)[C:3](=[S:4])[NH:2][CH3:1]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 4311764Sodium borohydrideHCID 19972906HCID 19972906, compound

Product 1

HCID 19972905HCID 19972905, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

19.09 g of the N-methyl-1-(4-methylimidazol-1-yl) 2-oxocyclohexanecarbothioamide prepared in the Preparative Example 2 was suspended in 290 ml of methanol. The obtained suspension was stirred under cooling with ice, followed by the addition of 1.44 g of sodium borohydride. The reaction mixture was analyzed by silica gel thin-layer chromatography (developer: a 10:1 mixture of chloroform and methanol). The product was a mixture comprising a lower-polarity diastereomer (L-form) as the main product and a higher-polarity one (M-form). After 30 minutes, the reaction mixture was concentrated to about 70 ml, followed by the addition of about 200 ml of water. The precipitate formed was recovered by filtration and washed with water to give 11.85 g of the title compound as a white solid (yield: 62%).

Workup

  1. temperatureunder cooling with ice
  2. concentrationthe reaction mixture was concentrated to about 70 ml
  3. additionfollowed by the addition of about 200 ml of water
  4. customThe precipitate formed
  5. filtrationwas recovered by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-6a15039e517a4cd99288b7b0b3b6facf
Source dataset
uspto-grants-1997_02
Patent number
US05605907

Reaction notes

Loading…