2-Isopropylaniline → HCID 178438957, compound

HRID 574319Notes

Reaction equation

HRID 574319 reaction equation
CO[C:3](=[O:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]=[C:11]=[S:12].[CH:14]([C:17]1[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=1[NH2:19])([CH3:16])[CH3:15]>CC(O)C.C[O-].[Na+]>[CH:14]([C:17]1[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=1[N:19]1[C:3](=[O:13])[C:4]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:10]=[C:11]1[SH:12])([CH3:16])[CH3:15]

Participants

5

Reactant 2

HCID 125612-IsopropylanilineHCID 85243Benzoic acid, 2-isothiocyanato-, methyl ester

Product 1

HCID 178438957HCID 178438957, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 10942334Sodium MethoxideCatalystHCID 3776IsopropanolSolvent

Procedure

2-Isothiocyanato-benzoic acid methyl ester (0.58 mL, 3.69 mmol) was added to a solution of 2-isopropyl aniline (500 mg, 3.69 mmol) and sodium methoxide (10 mg) in 2-propanol (10 mL) at room temperature and heated at reflux for 16 hr. The reaction mixture was concentrated to dryness under vacuum. The crude material was washed with dichloromethane (2×10 mL), 10% methanol in chloroform (2×10 mL) and dried under reduced pressure to afford 3-(2-isopropyl-phenyl)-2-mercapto-3H-quinazolin-4-one (600 mg, 55%) as white solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 16 hr
  3. concentrationThe reaction mixture was concentrated to dryness under vacuum
  4. washThe crude material was washed with dichloromethane (2×10 mL), 10% methanol in chloroform (2×10 mL)
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-c8aba986f5c34a158952580e0f8a9e29
Source dataset
uspto-grants-2015_05
Patent number
US09034887B2

Reaction notes

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