3-Nitroaniline → HCID 22060746, compound

HRID 1474882Notes

Reaction equation

HRID 1474882 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.[N+:10]([C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][CH:19]=1)[NH2:16])([O-:12])=[O:11]>CO.O>[N+:10]([C:13]1[CH:14]=[C:15]([NH:16][C:2]2[N:7]=[C:6]([NH:16][C:15]3[CH:17]=[CH:18][CH:19]=[C:13]([N+:10]([O-:12])=[O:11])[CH:14]=3)[C:5]([F:9])=[CH:4][N:3]=2)[CH:17]=[CH:18][CH:19]=1)([O-:12])=[O:11]

Participants

5

Reactant 2

HCID 74233-NitroanilineHCID 2507052,4-Dichloro-5-fluoropyrimidine

Product 1

HCID 22060746HCID 22060746, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

2,4-Dichloro-5-fluoropyrimidine (4.7 g, 28.1 mmol) was dissolved in a mixture of MeOH (150 ml) and H2O (15 ml). 3-nitroaniline (15.5 g, 112 mmol) was added and the mixture was refluxed for 20 hours (100° C. oil-bath temperature). The mixture was cooled to 22° C. and filtered. The residue was washed carefully with 200 ml MeOH—H2O (1:1; v/v) and dried under vacuum to give 7.89 g (76%) of N2,N4-bis(3-nitrophenyl)-5-fluoro-2,4-pyrimidinediamine as yellow crystals. 1H NMR (DMSO-d6+D2O): δ 8.63 (m, 2H), 8.21 (m, 1H), 8.08 (d, 1H, J=8.41 Hz), 7.88 (d, 1H, J=8.4 Hz), 7.79 (d, 1H, J=8.4 Hz), 7.70 (d, 1H, J=8.4 Hz), 7.57 (d, 1H, J=8.4 Hz), 7.45 (t, 1H, J=8.4 Hz); LCMS: purity: 100%; MS (m/e): 371.30 (M+, 100).

Workup

  1. temperatureThe mixture was cooled to 22° C.
  2. filtrationfiltered
  3. washThe residue was washed carefully with 200 ml MeOH—H2O (1:1; v/v)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-680d712833d1424e8d65eb8f2fef856f
Source dataset
uspto-grants-2015_04
Patent number
US09018204B1

Reaction notes

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