Benzoyl chloride → HCID 21313356, compound

HRID 2397500Notes

Reaction equation

HRID 2397500 reaction equation
[CH3:1][N:2]([CH3:10])[C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.C(Cl)(=O)C1C=CC=CC=1.CN(C)C1C=CC([NH:28][C:29](=[O:36])[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=CC=1.[H-].[Na+].[Na].NCl>CN(C=O)C.N1C=CC=CC=1>[C:29]([NH:28][NH:7][C:6]1[CH:8]=[CH:9][C:3]([N:2]([CH3:10])[CH3:1])=[CH:4][CH:5]=1)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

9

Reactant 6

HCID 7412Benzoyl chlorideHCID 7472N,N-dimethyl-p-phenylenediamineHCID 24758Sodium hydrideHCID 25423MonochloramineHCID 585572HCID 585572, compoundHCID 5360545Sodium

Product 1

HCID 21313356HCID 21313356, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

Reaction of 4-dimethylaminoaniline with benzoyl chloride in the presence of pyridine and reaction of the resulting N-(4-dimethylaminophenyl)benzamide with sodium hydride in DMF followed by reaction of the resulting sodium salt with chloramine all according to the procedure described above in Example 65 affords N'-benzoyl-4-dimethylaminophenylhydrazine. Reaction of the latter with 3-phthalimidopropyl methyl ketone in refluxing ethanol using the procedure described above in Example 1 affords 1-benzoyl-5-dimethylamino-2-methyl-3-(2-phthalimidoethyl)indole, which on refluxing in ethylene glycol dimethyl ether in the presence of a molar excess of hydrazine hydrate affords 1-benzoyl-3-(2-amimoethyl)-5-dimethylamino-2-methylindole. The latter, on reaction with one mole of isopropyl bromide in refluxing acetone in the presence of sodium carbonate affords 1-benzoyl-3-(2-isopropylaminoethyl)-5-dimethylamino-2-methylindole.

Sources & evidence

ORD record
ord-202fa870018547c7864ef96b46da0782
Source dataset
uspto-grants-1977_05
Patent number
US04021431

Reaction notes

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