4-Nitrobenzoyl chloride → HCID 20352248, compound

HRID 371940Notes

Reaction equation

HRID 371940 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]23[CH2:13][CH:12]2[CH2:11][NH:10][CH2:9]3)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[N+:20]([C:23]1[CH:31]=[CH:30][C:26]([C:27](Cl)=[O:28])=[CH:25][CH:24]=1)([O-:22])=[O:21]>C1C=CC=CC=1.O>[N+:20]([C:23]1[CH:24]=[CH:25][C:26]([C:27]([N:10]2[CH2:11][CH:12]3[C:8]([C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=4)([CH2:13]3)[CH2:9]2)=[O:28])=[CH:30][CH:31]=1)([O-:22])=[O:21]

Participants

6

Reactant 3

HCID 85024-Nitrobenzoyl chlorideHCID 10340Sodium CarbonateHCID 101303311-(4-Chlorophenyl)-3-azabicyclo[3.1.0]hexane

Product 1

HCID 20352248HCID 20352248, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 962WaterSolvent

Procedure

A 19.35 g. portion of 1-p-chlorophenyl-3-azabicyclo[3.1.0]hexane is dissolved in 150 ml. of benzene. A 10.59 g. portion of sodium carbonate in 100 ml. of water is added with stirring. An 18.45 g. portion of p-nitrobenzoyl chloride in 100 ml. of benzene is added slowly to the rapidly stirred mixture. The mixtue is stirred for 1 hour and then allowed to stand overnight at room temperature. The product is recovered by filtration, washed successively with dilute sodium carbonate, 0.5N hydrochloric acid and then water and dried yielding the product as a white solid, mp 177°-180° C.

Workup

  1. stirringThe mixtue is stirred for 1 hour
  2. filtrationThe product is recovered by filtration
  3. washwashed successively with dilute sodium carbonate, 0.5N hydrochloric acid
  4. dry with materialwater and dried

Sources & evidence

ORD record
ord-cc6c7cffa71440cea8ab2e2c4ec6ea6f
Source dataset
uspto-grants-1978_05
Patent number
US04088652

Reaction notes

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