4-Nitrobenzoyl chloride → HCID 178521933, compound

HRID 1450382

Reaction equation

HRID 1450382 reaction equation
[NH:1]1[C:5]([C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[NH2:8])=[N:4][N:3]=[N:2]1.NC1C=CC=CC=1C#N.[N-]=[N+]=[N-].[Na+].[N+:26]([C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1)([O-:28])=[O:27]>ClCCl.N1C=CC=CC=1>[N+:26]([C:29]1[CH:30]=[CH:31][C:32]([C:33]([NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[C:5]2[NH:1][N:2]=[N:3][N:4]=2)=[O:34])=[CH:36][CH:37]=1)([O-:28])=[O:27]

Participants

7

Reactant 4

HCID 85024-Nitrobenzoyl chlorideHCID 33557Sodium AzideHCID 729132-AminobenzonitrileHCID 178507487HCID 178507487, compound

Product 1

HCID 178521933HCID 178521933, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

3.0 g (18.6 mmol) 2-(tetrazol-5-yl)aniline (prepared by heating of 2-aminobenzonitrile in the presence of sodium azide according to E. R. Wagner, J. Org. Chem. 1973, 38, 2976) and 3.2 ml pyridine were dissolved in 50 ml dichloromethane. A solution of 3.7 g (19.9 mmol) 4-nitrobenzoyl chloride in 50 ml dichloromethane was added via a dropping funnel, and the mixture was heated with reflux for 1 h. The title compound precipitated from the solution, was filtered with suction, washed with hexane, and dried in vacuo to give a yellow powder, m.p. 223-225 (dec.)

Workup

  1. temperaturethe mixture was heated
  2. temperaturewith reflux for 1 h
  3. customThe title compound precipitated from the solution
  4. filtrationwas filtered with suction
  5. washwashed with hexane
  6. customdried in vacuo
  7. customto give a yellow powder, m.p. 223-225 (dec.)

Sources & evidence

ORD record
ord-04a26cd00929401a97f5a4c506827270
Source dataset
uspto-grants-1997_02
Patent number
US05602137

Linked notes

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