2,4-Dichlorobenzoyl chloride → 2,4-dichloro-N-[4-chloro-6-(4-chlorophenylamino)-pyrimidin-5-yl]-benzamide

HRID 1246779

Reaction equation

HRID 1246779 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[C:3]=1[NH2:16].[Cl:17][C:18]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21]>N1C=CC=CC=1>[Cl:17][C:18]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:19]=1[C:20]([NH:16][C:3]1[C:2]([Cl:1])=[N:7][CH:6]=[N:5][C:4]=1[NH:8][C:9]1[CH:10]=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=1)=[O:21]

Participants

4

Reactant 2

HCID 666452,4-Dichlorobenzoyl chlorideHCID 167263116-Chloro-N4-(4-chlorophenyl)pyrimidine-4,5-diamine

Product 1

HCID 219058382,4-dichloro-N-[4-chloro-6-(4-chlorophenylamino)-pyrimidin-5-yl]-benzamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

6-Chloro-N4-(4-chlorophenyl)-pyrimidine-4,5-diamine I-(1A-1)a (34 g, 134 mmol) in pyridine (150 ml) was cooled to 0° C. and to it was added 2,4-dichlorobenzoyl chloride (25 ml, 178 mmol). The reaction was allowed to warm to ambient temperature overnight. The solid precipitate was collected by vacuum filtration and dried under high vacuum to yield the title compound I-(1A-1)b as a colorless solid (14 g, 25%). The pyridine solution was concentrated under reduced pressure and then triturated with methanol (500 ml) to provide additional material (35 g, 60%): +ESI MS (M+1) 427.4; 1H NMR: (400 MHz, DMSO-d6): δ 10.08 (s, 1H), 9.16 (s, 1H), 8.38 (s, 1H), 7.97 (d, J=8.7 Hz, 1H), 7.75 (d, J=2.0 Hz, 2H), 7.64–7.60 (m, 3H), 7.40 (d, J=8.7 Hz, 2H).

Workup

  1. filtrationThe solid precipitate was collected by vacuum filtration
  2. customdried under high vacuum

Sources & evidence

ORD record
ord-2e84fe40d4d7488f8d26f2bb1084dfd2
Source dataset
uspto-grants-2006_10
Patent number
US07129239B2

Linked notes

Loading…