Benzene → HCID 21390841, compound

HRID 1730182Notes

Reaction equation

HRID 1730182 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][N:6]1[NH:10][CH:9]=[C:8]([C:11]2[N:12]([CH3:19])[C:13]([N+:16]([O-:18])=[O:17])=[CH:14][N:15]=2)[O:7]1.N1C=CC=CC=1.C1C=CC=CC=1>O>[C:1]([NH:5][N:6]1[NH:10][CH:9]=[C:8]([C:11]2[N:12]([CH3:19])[C:13]([N+:16]([O-:18])=[O:17])=[CH:14][N:15]=2)[O:7]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 241BenzeneHCID 1049PyridineHCID 6367Acetyl chlorideHCID 21390814HCID 21390814, compound

Product 1

HCID 21390841HCID 21390841, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Four grams of acetyl chloride are slowly added to 3.6 grams (0.017 mole) of 2-(2-amino-5-oxadiazolyl)-1-methyl-5-nitroimidazole suspended in a mixture of 44 ml. of pyridine and 35 ml. of benzene. The addition is completed in 30 minutes, the mixture heated at 60°-70° C. for 10 minutes, and then poured into 500 ml. of ice and water. After the resulting mixture is stirred for 1 1/2 hours, the product separates. Recrystallization from 150 ml. of acetone containing some N,N-dimethylformamide affords 2.4 grams (56%) of pale yellow product. A second recrystallization from acetone gives 2.1 g. of product, melting point 224°-225° C.

Workup

  1. additionsuspended in a mixture of 44 ml
  2. additionThe addition
  3. temperaturethe mixture heated at 60°-70° C. for 10 minutes
  4. additionpoured into 500 ml
  5. customRecrystallization from 150 ml

Sources & evidence

ORD record
ord-c2c8f6138d0e4d76a7477d0ae308cf5a
Source dataset
uspto-grants-1976_11
Patent number
US03991200

Reaction notes

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