[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]thiourea → HCID 25106116, compound

HRID 604933Notes

Reaction equation

HRID 604933 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]([NH2:18])=[S:17])[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1.Cl[CH2:20][C:21](=O)[C:22]([CH3:33])([C:24]1[CH:29]=[C:28]([F:30])[C:27]([F:31])=[C:26]([F:32])[CH:25]=1)[CH3:23]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]2[S:17][CH:20]=[C:21]([C:22]([CH3:33])([C:24]3[CH:25]=[C:26]([F:32])[C:27]([F:31])=[C:28]([F:30])[CH:29]=3)[CH3:23])[N:18]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1

Participants

4

Reactant 2

HCID 71650841[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]thioureaHCID 86624716HCID 86624716, compound

Product 1

HCID 25106116HCID 25106116, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 78.7 mg (0.3 mmol) [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea and of 90.2 mg (0.36 mmol) 1-chloro-3-methyl-3-(3,4,5-trifluoro-phenyl)-butan-2-one in ethanol (3 ml) was heated to reflux over night. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel using methylene chloride/methanol 19/1 to 9/1 as eluent to yield 95 mg (69%) of the title compound as a light yellow solid. MS ISP (m/e): 459.1 (100) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=10.38 (s, 1H), 7.83 (s, 1H), 7.63 (s, 1H), 7.23-7.18 (m, 3H), 7.01 (s, 1H), 6.88 (d, 1H), 6.69 (s, 1H), 3.68 (s, 3H), 2.13 (s, 3H), 1.65 (s, 6H).

Workup

  1. temperatureto reflux over night
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-33a2ddda133f4918b19ce4190a9f8ed6
Source dataset
uspto-grants-2011_03
Patent number
US07910740B2

Reaction notes

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