Carbon Tetrachloride → 5-(Chloro)carbonyl-6-nitro-1,3-benzodioxole

HRID 904632

Reaction equation

HRID 904632 reaction equation
[CH2:1]1[O:12][C:11]2[C:3](=[CH:4][C:5]([N+:13]([O-:15])=[O:14])=[C:6]([CH:10]=2)[C:7](O)=[O:8])[O:2]1.P(Cl)(Cl)(Cl)(Cl)[Cl:17].C(Cl)(Cl)(Cl)Cl>C1CCCCC1>[CH2:1]1[O:12][C:11]2[C:3](=[CH:4][C:5]([N+:13]([O-:15])=[O:14])=[C:6]([CH:10]=2)[C:7]([Cl:17])=[O:8])[O:2]1

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 24819Phosphorus pentachlorideHCID 2464356-Nitro-1,3-benzodioxole-5-carboxylic acid

Product 1

HCID 155638945-(Chloro)carbonyl-6-nitro-1,3-benzodioxole

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

Reaction of 31.7 g of 4,5-methylenedioxy-2-nitrobenzoic acid and 31.2 g of phosphorus pentachloride in 250 ml of cylohexane at reflux for 30 minutes followed by treatment of the crude oil twice with carbon tetrachloride gave 4,5-methylenedioxy-2-nitrobenzoyl chloride. The acid chloride was dissolved in 50 ml of tetrahydrofuran and added to a warm solution of 30.9 g of 5-aminotetrazole monohydrate in 750 ml of tetrahydrofuran and 30 ml of water. The solution was stirred for 30 minutes and then diluted with 3 liters of water. The solid which formed was separated by filtration and dried to give 4,5-methylenedioxy-2-nitro-N-(1H-tetrazol-5-yl)benzamide melting at about 279° C. after recrystallization from a mixture of dimethylformamide and water.

Workup

  1. temperatureat reflux for 30 minutes

Sources & evidence

ORD record
ord-36e294c3d1e64ccca60558cebb6a3695
Source dataset
uspto-grants-1983_12
Patent number
US04419357

Linked notes

Loading…