HCID 54522606, compound → HCID 23460560, compound

HRID 2286980Notes

Reaction equation

HRID 2286980 reaction equation
[Cl:1][C:2]1[CH:35]=[CH:34][C:5]([C:6]([N:8]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N+:15]([O-])=O)=O)=[CH:4][C:3]=1[N+:36]([O-])=O>C(O)C.O.Cl.[Fe]>[Cl:1][C:2]1[CH:35]=[CH:34][C:5]([C:6]2[N:8]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:15]=2)=[CH:4][C:3]=1[NH2:36]

Participants

6

Reactant 1

HCID 54522606HCID 54522606, compound

Product 1

HCID 23460560HCID 23460560, compoundYield 88.9%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 313Hydrochloric AcidSolvent2×HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of 42 g of N-(4-chloro-3-nitrobenzoyl)N-n-hexadecyl-2-nitro-aniline in 700 ml of ethanol is allowed to run rapidly into a mixture, which has been heated to 60° C., of 89 g of iron powder in 120 ml of water and 40 ml of concentrated hydrochloric acid, with vigorous stirring. The reaction mixture is then stirred for four hours at the reflux temperature. A further 100 ml of concentrated hydrochloric acid and 200 ml of ethanol are then added and the mixture is filtered hot. About 400 ml of ethanol are then distilled off and the residue is left to crystallise out at 4° C. After filtering and drying, 32 g of the compound are obtained in the form of the hydrochloride with a melting point of 162° to 163° C.

Workup

  1. filtrationthe mixture is filtered hot
  2. distillationAbout 400 ml of ethanol are then distilled off
  3. waitthe residue is left
  4. customto crystallise out at 4° C
  5. filtrationAfter filtering
  6. customdrying

Sources & evidence

ORD record
ord-07008b3e04d74d42ac606d549d825bef
Source dataset
uspto-grants-1981_05
Patent number
US04268591

Reaction notes

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