Water → HCID 53698436, compound

HRID 1030245Notes

Reaction equation

HRID 1030245 reaction equation
[CH:1]([CH:3]=[C:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C:5]1([C:14]1[CH:15]=[N:16][C:17]2[C:22]([CH:23]=1)=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:10](=[S:13])[NH:11][CH3:12])=[O:2].[BH4-].[Na+].C(OCC)(=O)C.O>CO>[OH:2][CH2:1][CH:3]=[C:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C:5]1([C:14]1[CH:15]=[N:16][C:17]2[C:22]([CH:23]=1)=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:10](=[S:13])[NH:11][CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 57246350HCID 57246350, compound

Product 1

HCID 53698436HCID 53698436, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (±)-2 -formylmethylene-N-methyl-1-(quinolin-3 -yl)cyclohexane carbothioamide (150 mg, 0.46 mmol) at room temperature in methanol (5 ml) was treated with sodium borohydride (20 mg, 0.5 mmol). The mixture was stirred at room temperature for 45 mins. Ethyl acetate (20 ml) and then water (20 ml) were added to the reaction mixture. The layers were separated and the organic extract was dried over magnesium sulphate. Concentration in vacuo yielded a crude solid which was purified by flash chromatography over silica gel, eluting with a 1:1 (v/v) mixture of ethyl acetate/hexane to yield (±)-2 -hydroxyethylidene-N-methyl-1-(quinolin-3-yl) cyclohexane carbothioamide (100 mg, 0.31 mmol) as a white solid, m.p. 104°-110° C.;

Workup

  1. customThe layers were separated
  2. extractionthe organic extract
  3. dry with materialwas dried over magnesium sulphate
  4. concentrationConcentration in vacuo
  5. customyielded a crude solid which
  6. customwas purified by flash chromatography over silica gel
  7. washeluting with a 1:1 (v/v) mixture of ethyl acetate/hexane

Sources & evidence

ORD record
ord-60e2b7c35bf14bc1bc8cc2a73e2ddca0
Source dataset
uspto-grants-1992_04
Patent number
US05104883

Reaction notes

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