Dichloromethane → 5-Methyl-2-nitrobenzoyl chloride

HRID 904628

Reaction equation

HRID 904628 reaction equation
[CH3:1][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>C1(C)C=CC=CC=1>[CH3:1][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 6344DichloromethaneHCID 183715-Methyl-2-nitrobenzoic acidHCID 24819Phosphorus pentachloride

Product 1

HCID 30160135-Methyl-2-nitrobenzoyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The reaction of 36.2 g of 5-methyl-2-nitrobenzoic acid and 41.6 g of phosphorus pentachloride in 150 ml of toluene gave a crude product which was treated with methylene chloride to give 5-methyl-2-nitrobenzoyl chloride as an oil. When 30 g of this acid chloride in 50 ml of tetrahydrofuran was added to a warm solution of 30.9 g of 5-aminotetrazole monohydrate in 600 ml of tetrahydrofuran and 30 ml of water, a precipitate formed quickly. This was allowed to stand for 1 hour, the white solid was separated by filtration, washed with water and air dried to give 5-methyl-2-nitro-N-(1H-tetrazol-5-yl)benzamide melting at about 278°-279° C.

Workup

  1. customgave a crude product which

Sources & evidence

ORD record
ord-a06f52ea2f434a8483b1c3bd8ca9c798
Source dataset
uspto-grants-1983_12
Patent number
US04419357

Linked notes

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