Thionyl Chloride → 4-bromo-N-(4-chloro-phenyl)-benzimidoyl chloride

HRID 1024627Notes

Reaction equation

HRID 1024627 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=O)=[CH:4][CH:3]=1.S(Cl)([Cl:20])=O.BrC1C=CC(C2N(C3C=CC(Cl)=CC=3)C(=O)C3C=NN(C4C=CC=C(SC)C=4)C=3N=2)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([Cl:20])=[N:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 774372HCID 774372, compoundHCID 247816196-(4-Bromo-phenyl)-5-(4-chloro-phenyl)-1-(3-methylsulfanyl-phenyl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

Product 1

HCID 578981714-bromo-N-(4-chloro-phenyl)-benzimidoyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
170 °C

Procedure

4-Bromo-N-(4-chloro-phenyl)-benzimidoyl chloride is prepared by heating 4-bromo-N-(4-chloro-phenyl)-benzamide (16.5 g, 53.0 mmol) and thionyl chloride (140 mL) for 1 h. The clear solution is concentrated and the residue obtained is coevaporated with toluene (100 mL). Then 5-amino-1-(3-methylsulfanyl-phenyl)-1H-imidazole-4-carboxylic acid ethyl ester (1, 9.8 g, 35.33 mmol) is added and the resulting mixture is heated to 170° C. with out solvent for 6 h. The crude product obtained is purified by column chromatography (6).

Workup

  1. concentrationThe clear solution is concentrated
  2. customthe residue obtained

Sources & evidence

ORD record
ord-6d535525cfcc4a3e846fdbe72fbfd2e7
Source dataset
uspto-grants-2014_05
Patent number
US08722691B2

Reaction notes

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