3-Methyl-2-nitrobenzoic acid → HCID 178425300, compound

HRID 904629Notes

Reaction equation

HRID 904629 reaction equation
[CH3:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](O)=[O:6].P(Cl)(Cl)(Cl)(Cl)Cl.CC1C([N+]([O-])=O)=C(C=CC=1)C(Cl)=O.O.[NH2:34][C:35]1[NH:39][N:38]=[N:37][N:36]=1>C1CCCCC1.O1CCCC1.O.C(Cl)Cl>[CH3:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH:34][C:35]1[NH:39][N:38]=[N:37][N:36]=1)=[O:6]

Participants

9

Reactant 4

HCID 215753-Methyl-2-nitrobenzoic acidHCID 24819Phosphorus pentachlorideHCID 2671613-methyl-2-nitrobenzoyl chlorideHCID 178509300HCID 178509300, compound

Product 1

HCID 178425300HCID 178425300, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×HCID 8078CyclohexaneSolvent

Procedure

The reaction of 50 g of 3-methyl-2-nitrobenzoic acid and 57.5 g of phosphorus pentachloride in 300 ml of cyclohexane gave, after treatment of the crude product with methylene chloride, 3-methyl-2-nitrobenzoyl chloride melting at about 81°-82° C. A solution of 53.1 g of this acid chloride and 50 ml of tetrahydrofuran was added to a warm solution of 55 g of 5-aminotetrazole monohydrate in 500 ml of tetrahydrofuran and 20 ml of water. The reaction was exothermic, a white precipitate formed and the mixture was allowed to stand for 4 hours. It was then diluted with water, the white precipitate was separated by filtration, washed with water and air dried to give 3-methyl-2-nitro-N-(1H-tetrazol-5-yl)benzamide melting at about 262°-263° C., with decomposition, after recrystallization from a mixture of dimethylformamide and water.

Workup

  1. customgave
  2. customa white precipitate formed
  3. customthe white precipitate was separated by filtration
  4. washwashed with water and air
  5. customdried

Sources & evidence

ORD record
ord-12fbb0647c024b59b6f23db918b3e356
Source dataset
uspto-grants-1983_12
Patent number
US04419357

Reaction notes

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