Toluene → 4-bromo-N-(4-chloro-phenyl)-benzimidoyl chloride

HRID 1024615Notes

Reaction equation

HRID 1024615 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.C1(C)C=CC=CC=1.BrC1C=CC(C2N(C3C=CC(Cl)=CC=3)C(=O)C3C=NN(C4C=CC=C(SC)C=4)C=3N=2)=CC=1>C(Cl)(Cl)Cl>[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

6

Reactant 4

HCID 1140TolueneHCID 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 6212ChloroformSolvent

Conditions

Temperature
170 °C

Procedure

4-Bromo-N-(4-chloro-phenyl)-benzimidoyl chloride is prepared by heating 4-bromo-N-(4-chloro-phenyl)-benzamide (13.39 g, 43.2 mmol) and thionyl chloride (100 mL) for 1 h. The clear solution is concentrated and the residue obtained is coevaporated with toluene (100 mL). A solution of 5-amino-1-(3-nitro-phenyl)-1H-imidazole-4-carboxylic acid ethyl ester (1, 4.00 g, 14.4 mmol) in dry chloroform (50 mL) is then added and the resulting mixture is concentrated to afford a dry residue. It is heated to 170° C. with out solvent for 6 h. The crude product obtained is purified by column chromatography to afford the product as greenish black solid as product (6).

Workup

  1. concentrationThe clear solution is concentrated
  2. customthe residue obtained
  3. concentrationthe resulting mixture is concentrated
  4. customto afford a dry residue
  5. customThe crude product obtained

Sources & evidence

ORD record
ord-f7124ceec37c4dfc9cad4c1a96501fb1
Source dataset
uspto-grants-2014_05
Patent number
US08722691B2

Reaction notes

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