N,N-Dimethylaniline → HCID 12766135, compound

HRID 1194875Notes

Reaction equation

HRID 1194875 reaction equation
Cl[CH2:2][C:3](=O)/[C:4](=[N:10]/[O:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)/[C:5]([O:7][CH2:8][CH3:9])=[O:6].CN(C)C1C=CC=CC=1.[NH2:28][C:29]([NH2:31])=[S:30]>C(O)C>[NH2:31][C:29]1[S:30][CH:2]=[C:3](/[C:4](=[N:10]/[O:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)/[C:5]([O:7][CH2:8][CH3:9])=[O:6])[N:28]=1

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 2723790ThioureaHCID 88627674HCID 88627674, compound

Product 1

HCID 12766135HCID 12766135, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 4-chloro-(Z)-2-(cyclohexyloxyimino)-3-oxobutyrate (0.68 g) was dissolved in ethanol (6 ml) and N,N-dimethylaniline (0.30 g) and thiourea (0.19 g) added with stirring. After 18 h the mixture was evaporated and the residue partitioned between dichloromethane and water. The organic layer was separated, washed with brine, dried (MgSO4) and evaporated. Purification by flash chromatography eluting with ethyl acetate/hexane gave the title compound as a cream solid (0.66 g, 90%). A sample was crystallised from cyclohexane, m.p. 133°-4° C.; νmax (CHCl3) 2940, 1730, 1605 cm-1 ; δH (CDCl3) 1.34 (3H, t), 1.3-2.0 (10H, br m), 4.3 (1H, br m), 4.36 (2H, q), 5.4 (2H, br s, exch D2O), and 6.68 (1H, s).

Workup

  1. customAfter 18 h the mixture was evaporated
  2. customthe residue partitioned between dichloromethane and water
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customPurification by flash chromatography
  8. washeluting with ethyl acetate/hexane

Sources & evidence

ORD record
ord-f40a3306e2924665ad879c943fd2abf3
Source dataset
uspto-grants-1989_03
Patent number
US04816452

Reaction notes

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