Phenothiazine → 10-[3-(Imidazol-1-yl)-propionyl]-phenothiazine

HRID 1577826Notes

Reaction equation

HRID 1577826 reaction equation
[CH:1]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[N:15]1([CH2:20][CH2:21][C:22](O)=[O:23])[CH:19]=[CH:18][N:17]=[CH:16]1.C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)C>[N:15]1([CH2:20][CH2:21][C:22]([N:13]2[C:14]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[S:6][C:7]3[C:12]2=[CH:11][CH:10]=[CH:9][CH:8]=3)=[O:23])[CH:19]=[CH:18][N:17]=[CH:16]1

Participants

5

Reactant 3

HCID 7108PhenothiazineHCID 10868DicyclohexylcarbodiimideHCID 27947183-(1H-imidazol-1-yl)propanoic acid

Product 1

HCID 2056977110-[3-(Imidazol-1-yl)-propionyl]-phenothiazine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 19.9 g of phenothiazine, 14 g of 3-(imidazol-1-yl)-propionic acid, 20.6 g of dicyclohexylcarbodiimide, and 200 ml of ethyl acetate is stirred for 30 minutes at 0°, and then for 3 hours at 20°. It is worked up in the customary manner to give 10-[3-(imidazol-1-yl)-propionyl]-phenothiazine, melting point 150°-152°.

Workup

  1. waitfor 3 hours at 20°

Sources & evidence

ORD record
ord-4be27e812e3a40ad9354db59caa194d5
Source dataset
uspto-grants-1981_09
Patent number
US04289768

Reaction notes

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