Hydrochloric Acid → 6-Chloro-N4-(4-chlorophenyl)pyrimidine-4,5-diamine

HRID 1246778

Reaction equation

HRID 1246778 reaction equation
[NH2:1][C:2]1[C:3]([Cl:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[Cl:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1.Cl>O.C(O)C>[Cl:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([NH:15][C:14]2[CH:16]=[CH:17][C:11]([Cl:10])=[CH:12][CH:13]=2)[C:2]=1[NH2:1]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 78124-ChloroanilineHCID 794345-Amino-4,6-dichloropyrimidine

Product 1

HCID 167263116-Chloro-N4-(4-chlorophenyl)pyrimidine-4,5-diamineYield 99.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

5-amino-4,6-dichloropyrimidine (5.00 g, 29 mmol) and 4-chloroaniline (4.71 g, 36 mmol) were suspended in 80 ml H2O and 12 ml ethanol. Concentrated HCl (1.2 ml, 14.5 mmol) was added at room temperature followed by warming reaction to 82° C. After stirring for 19 hours the reaction was cooled to room temperature and stirred for 60 hours. The precipitate was collected on a sintered glass funnel and rinsed with water followed by hexanes. After drying under vacuum, I-(1A-1)a was obtained as an off-white solid (7.38 g, 98%): +ESI MS (M+1) 255.3; 1H NMR: (400 MHz, CD3OD): δ 7.87 (s, 1H), 7.66 (d, J=8.7 Hz, 2 H), 7.30 (d, J=8.7 Hz, 2 H).

Workup

  1. temperatureby warming
  2. customreaction to 82° C
  3. stirringstirred for 60 hours
  4. customThe precipitate was collected on a sintered glass funnel
  5. washrinsed with water
  6. customAfter drying under vacuum

Sources & evidence

ORD record
ord-93a9f1f639764b5b8afb51c603527d38
Source dataset
uspto-grants-2006_10
Patent number
US07129239B2

Linked notes

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