4-Cyanobenzoyl chloride → HCID 19921297, compound

HRID 1647893Notes

Reaction equation

HRID 1647893 reaction equation
Cl.[CH3:2][O:3][C:4]([CH2:6][CH2:7][NH:8][C:9](=[O:27])[C:10]1[CH:15]=[CH:14][C:13]([NH:16][CH2:17][CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][S:23][CH2:22][CH2:21]2)=[C:12]([NH2:26])[CH:11]=1)=[O:5].[C:28]([C:30]1[CH:38]=[CH:37][C:33]([C:34](Cl)=O)=[CH:32][CH:31]=1)#[N:29]>C(O)(=O)C>[C:28]([C:30]1[CH:38]=[CH:37][C:33]([C:34]2[N:16]([CH2:17][CH2:18][CH2:19][N:20]3[CH2:25][CH2:24][S:23][CH2:22][CH2:21]3)[C:13]3[CH:14]=[CH:15][C:10]([C:9]([NH:8][CH2:7][CH2:6][C:4]([O:3][CH3:2])=[O:5])=[O:27])=[CH:11][C:12]=3[N:26]=2)=[CH:32][CH:31]=1)#[N:29]

Participants

4

Reactant 2

HCID 801724-Cyanobenzoyl chlorideHCID 67806829HCID 67806829, compound

Product 1

HCID 19921297HCID 19921297, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

48.6 g of 3-amino-4-(3-thiomorpholino-propylamino)-benzoic acid-[N-(2-methoxycarbonyl-ethyl)-amide]-hydrochloride are dissolved in 500 ml of glacial acetic acid with heating, 19.5 g of 4-cyano-benzoylchloride are added, the mixture is heated for one hour over a steam bath and a further 2 hours at a bath temperature of 120° C. The mixture is evaporated down in vacuo and the residue is purified by chromatography on silica gel (eluant:methylene chloride/methanol/conc. ammonia=9:1:0 to 8:2:0.2). Yield: 33.7 g (58% of theory), Rf value: 0.84 (silica gel; methylene chloride/methanol/conc. ammonia=19:1:0.1, after developing three times)

Workup

  1. temperaturewith heating
  2. customThe mixture is evaporated down in vacuo
  3. customthe residue is purified by chromatography on silica gel (eluant:methylene chloride/methanol/conc. ammonia=9:1:0 to 8:2:0.2)

Sources & evidence

ORD record
ord-4668f13340fc4441b7c38981970340b4
Source dataset
uspto-grants-1995_07
Patent number
US05434150

Reaction notes

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