Toluene → 3-Methoxy-2-nitrobenzoyl chloride
Reaction equation
[CH3:1][O:2][C:3]1[C:4]([N+:12]([O-:14])=[O:13])=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](O)=[O:7].P(Cl)(Cl)(Cl)(Cl)[Cl:16].C1(C)C=CC=CC=1>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:4]([N+:12]([O-:14])=[O:13])=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([Cl:16])=[O:7]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Reaction of 30 g of 3-methoxy-2-nitrobenzoic acid and 31.6 g of phosphorus pentachloride in 400 ml of methylene chloride at reflux for 2 hours followed by treatment of the crude product obtained with toluene 3 times gave 3-methoxy-2-nitrobenzoyl chloride as a solid. A solution of 30 g of this acid chloride in 50 ml of tetrahydrofuran was added to a solution of 28.7 g of 5-aminotetrazole monohydrate in 300 ml of tetrahydrofuran and 15 ml of water. A white precipitate appeared immediately but the mixture was allowed to stand for 3 hours. It was then diluted with water and the white solid was separated by filtration and air dried to give 3-methoxy-2-nitro-N-(1H-tetrazol-5-yl)benzamide melting at about 271° C. after recrystallization from dimethylformamide.
Workup
- temperatureat reflux for 2 hours
Sources & evidence
- ORD record
- ord-a969aa1fc5624854b55518935ac4625b
- Source dataset
- uspto-grants-1983_12
- Patent number
- US04419357
Reaction notes
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