4-(Methylthio)aniline → HCID 42625835, compound

HRID 1668786Notes

Reaction equation

HRID 1668786 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:12])[N:3]=1.[CH3:13][S:14][C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1.C([O-])(=O)C.[Na+]>C(OCC)(=O)C>[CH3:13][S:14][C:15]1[CH:21]=[CH:20][C:18]([NH:19][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[C:4]([CH3:12])[N:3]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 660384-(Methylthio)anilineHCID 517045Sodium AcetateHCID 27854214-Chloro-2-methylquinazoline

Product 1

HCID 42625835HCID 42625835, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 4-chloro-2-methyl-quinazoline (178.6 mg, 1.0 mmol), 4-methylthio-aniline (139.2 mg, 1.0 mmol) and sodium acetate (98.4 mg, 1.20 mmol) in 4 mL of solvent (THF:water=1:1) was stirred at 60-70° C. for 3 h. The reaction mixture was diluted with 30 mL of ethyl acetate. It was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated. The crude product was rinsed with ethyl acetate and dried, yielding 273 mg of title compound (97.2%). 1H NMR (CDCl3): 7.86-7.82 (m, 2H), 7.79-7.73 (m, 3H)), 7.50-7.45 (m, 2H), 7.34-7.26 (m, 2H), 2.7 (s, 3H), 2.51 (s, 3H),

Workup

  1. washIt was washed with brine
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washThe crude product was rinsed with ethyl acetate
  6. customdried

Sources & evidence

ORD record
ord-73374adf082b44aa93faa7fcb64072eb
Source dataset
uspto-grants-2011_08
Patent number
US07989462B2

Reaction notes

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