O-Xylene → HCID 19428228, compound

HRID 1078615Notes

Reaction equation

HRID 1078615 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[N:14]=[C:15]([NH:19][C:20]([NH2:22])=[S:21])[S:16][C:17]=3[CH3:18])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:23][O:24][C:25]1[CH:30]=[C:29]([CH3:31])[C:28]([S:32](N)(=[O:34])=[O:33])=[C:27]([CH3:36])[CH:26]=1.C(=O)([O-])[O-].[K+].[K+].C1(C)C(C)=CC=CC=1>C(OCC)(=O)C>[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]([C:13]3[N:14]=[C:15]([NH:19][C:20]([NH:22][S:32]([C:28]4[C:29]([CH3:31])=[CH:30][C:25]([O:24][CH3:23])=[CH:26][C:27]=4[CH3:36])(=[O:34])=[O:33])=[S:21])[S:16][C:17]=3[CH3:18])=[CH:11][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 7237O-XyleneHCID 11430Potassium CarbonateHCID 194282304-Methoxy-2,6-dimethylbenzenesulfonamideHCID 19428233HCID 19428233, compound

Product 1

HCID 19428228HCID 19428228, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-[4-(4-cyclohexylphenyl)-5-methyl-2-thiazolyl]thiourea (1.00 g), 4-methoxy-2,6-dimethylphenylsulfonamide (1.30 g), potassium carbonate (500 mg) and xylene (40 ml) was refiuxed with heating for 2 hours. After ethyl acetate (200 ml) was added, the mixture was washed with 2 N-hydrochloric acid and water and dried (magnesium sulfate), after which the solvent was distilled off. The residue was subjected to silica gel chromatography and eluted with methanol-chloroform (5:95, v/v) to yield a crystal of 1-[4-(4-cyclohexylphenyl)-5-methyl-2-thiazolyl]-3-(4-methoxy-2,6-dimethylphenylsulfonyl)-2-thiourea (890 mg, yield 56%). This product was recrystallized from dichloromethane-methanol to yield a colorless prismatic crystal.

Workup

  1. temperaturewith heating for 2 hours
  2. washthe mixture was washed with 2 N-hydrochloric acid and water
  3. dry with materialdried (magnesium sulfate)
  4. distillationafter which the solvent was distilled off
  5. washeluted with methanol-chloroform (5:95

Sources & evidence

ORD record
ord-f65250a5e54147d59723e63c97fd17d5
Source dataset
uspto-grants-1996_08
Patent number
US05550138

Reaction notes

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