Dichloromethane → HCID 178465510, compound

HRID 477407Notes

Reaction equation

HRID 477407 reaction equation
[CH2:1]([N:3]=[C:4]=[S:5])[CH3:2].[C:6]([C:10]1[C:11](=[O:27])[CH2:12][CH:13]([C:17]2[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[C:19]([NH2:25])[C:18]=2[CH3:26])[CH2:14][C:15]=1[OH:16])(=[O:9])[CH2:7][CH3:8].C(Cl)Cl>C(O)C>[C:6]([C:10]1[C:11](=[O:27])[CH2:12][CH:13]([C:17]2[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[C:19]([NH:25][C:4]([NH:3][CH2:1][CH3:2])=[S:5])[C:18]=2[CH3:26])[CH2:14][C:15]=1[OH:16])(=[O:9])[CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 10966Ethyl isothiocyanateHCID 178458842HCID 178458842, compound

Product 1

HCID 178465510HCID 178465510, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethylisothiocyanate (0.35 g, 3.98 mmol) was added to a solution of 2-propionyl-3-hydroxy-5-(3-amino-2,4,6-trimethylphenyl)cyclohex-2-en-1-one (1.0 g, 3.32 mmol) in ethanol (5 ml). Stirring was continued at 20° for 4 days. Dilute acid and methylene chloride were added. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated. The crude product was purified by chromatography on silica gel (elution with an increasing gradient of methanol in methylene chloride) to yield 2-propionyl-3-hydroxy-5-(3-ethylthioureido-2,4,6-trimethylphenyl)cyclohex-2-en-1-one as an oil (0.4 g, 33%). The compound was characterized by proton magnetic resonance spectroscopy (CDCl3, δ in ppm): 1.12 (6H,t); 2.18 (3H,s); 2.28 (3H,s); 2.39 (3H,s); 2.4-4.2 (9H,m); 5.4 (1H,brs); 6.29 (1H,s); 8.34 (1H,brs).

Workup

  1. additionwere added
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe crude product was purified by chromatography on silica gel (
  6. washelution with an increasing gradient of methanol in methylene chloride)

Sources & evidence

ORD record
ord-28bd655d732c4d27bdef00e0c1559e00
Source dataset
uspto-grants-1989_12
Patent number
US04888043

Reaction notes

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