Aniline → HCID 178516516, compound

HRID 347749Notes

Reaction equation

HRID 347749 reaction equation
CS[C:3]1[N:8]=[C:7]([OH:9])[CH:6]=[CH:5][N:4]=1.[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>COCCOCCOC>[NH:10]([C:3]1[N:8]=[C:7]([OH:9])[CH:6]=[CH:5][N:4]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 178503462HCID 178503462, compound

Product 1

HCID 178516516HCID 178516516, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
160 °C

Procedure

2-Methylthio-4-hydroxypyrimidine (1.42 g, 10 mmol) was dissolved in 2-methoxyethylether (10 ml). To this solution was added aniline (910 μl, 10 mmol) and the reaction mixture heated at 160° C. for 18 hours. The resulting precipitate was filtered off and washed with diethyl ether (10 ml), water (10 ml), diethyl ether (2×10 ml) and dried under vacuum to give the title product as a colourless solid (1.296 g, 69%). NMR (300 MHz): 5.79, (d, 1H), 6.99 (t, 1H), 7.24 (m, 2H), 7.57 (m, 2H), 7.73 (m, 1H), 8.80 (br, 1H); m/z: (ES+) 188.1 (MH+).

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. washwashed with diethyl ether (10 ml), water (10 ml), diethyl ether (2×10 ml)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-036c2fbdcc694d399a7c60e3ad928240
Source dataset
uspto-grants-2007_02
Patent number
US07176212B2

Reaction notes

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