Dicyclohexylcarbodiimide → 2-Chloro-10-[3-(imidazol-1-yl)-propionyl]-phenothiazine-5-oxide

HRID 1577827Notes

Reaction equation

HRID 1577827 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[S:12](=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[NH:5][C:4]=2[CH:3]=1.[N:17]1([CH2:22][CH2:23][C:24](O)=[O:25])[CH:21]=[CH:20][N:19]=[CH:18]1.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[S:12](=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]([C:24](=[O:25])[CH2:23][CH2:22][N:17]3[CH:21]=[CH:20][N:19]=[CH:18]3)[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 27947183-(1H-imidazol-1-yl)propanoic acidHCID 64513352-chloro-10H-phenothiazine 5-oxide

Product 1

HCID 205697972-Chloro-10-[3-(imidazol-1-yl)-propionyl]-phenothiazine-5-oxide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 25 g of 2-chloro-phenothiazine-5-oxide, 14 g of 3-(imidazol-1-yl)-propionic acid, 20.6 g of dicyclohexylcarbodiimide and 250 ml of tetrahydrofuran is stirred for 1 hour at 0° and then for 2 hours at 30°. It is worked up in the customary manner to give 2-chloro-10-[3-(imidazol-1-yl)-propionyl]-phenothiazine-5-oxide, melting point 148°-149°.

Workup

  1. waitfor 2 hours at 30°

Sources & evidence

ORD record
ord-7e3132de106e4942a3015d0e8f2a871e
Source dataset
uspto-grants-1981_09
Patent number
US04289768

Reaction notes

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