Carbon Tetrachloride → 5-Chloro-2-nitrobenzoyl chloride

HRID 904630Notes

Reaction equation

HRID 904630 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7](O)=[O:8].P(Cl)(Cl)(Cl)(Cl)[Cl:15].C(Cl)(Cl)(Cl)Cl>C1CCCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([Cl:15])=[O:8]

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 172865-Chloro-2-nitrobenzoic acidHCID 24819Phosphorus pentachloride

Product 1

HCID 27236855-Chloro-2-nitrobenzoyl chloride

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

Reaction of 100 g of 5-chloro-2-nitrobenzoic acid and 103.3 g of phosphorus pentachloride in 400 ml of cyclohexane at reflux for 80 minutes followed by treatment of the crude product 3 times with carbon tetrachloride gave 5-chloro-2-nitrobenzoyl chloride. A solution of the acid chloride in 50 ml of tetrahydrofuran was added to a warm solution of 91.3 g of 5-aminotetrazole monohydrate in 500 ml of tetrahydrofuran and 20 ml of water. A precipitate formed, and the mixture was allowed to stand for 4 hours. It was then diluted with water and the solid was separated by filtration and air dried to give 5-chloro-2-nitro-N-(1H-tetrazol-5-yl)benzamide melting at about 268°-269° C., after recrystallization from dimethylformamide.

Workup

  1. temperatureat reflux for 80 minutes

Sources & evidence

ORD record
ord-7da187c867734f44ac9c4fa4e5e0ecf1
Source dataset
uspto-grants-1983_12
Patent number
US04419357

Reaction notes

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