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

HRID 1577824Notes

Reaction equation

HRID 1577824 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)[N:5]([C:17](=[O:21])[CH2:18][CH2:19]Cl)[C:4]=2[CH:3]=1.ClC1C=CC2SC3C(=CC=CC=3)NC=2C=1.ClCCC(Cl)=O.ClC1C=CC2SC3C(=CC=CC=3)N(C(=O)CCCl)C=2C=1.OO.[NH:65]1[CH:69]=[CH:68][N:67]=[CH:66]1>C1C=CC=CC=1>[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:17](=[O:21])[CH2:18][CH2:19][N:65]3[CH:69]=[CH:68][N:67]=[CH:66]3)[C:4]=2[CH:3]=1

Participants

8

Reactant 6

HCID 784Hydrogen PeroxideHCID 795ImidazoleHCID 70882-ChlorophenothiazineHCID 693643-Chloropropionyl chlorideHCID 17131843-Chloro-1-(2-chloro-phenothiazin-10-yl)-propan-1-oneHCID 205696842-Chloro-10-(3-chloropropionyl)-phenothiazine-5-oxide

Product 1

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

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 68 g (0.2 mole) of 2-chloro-10-(3-chloropropionyl)-phenothiazine-5-oxide [obtainable by boiling 2-chlorophenothiazine with 3-chloropropionyl chloride in benzene for 12 hours and oxidizing the resulting 2-chloro-10-(3-chloropropionyl)-phenothiazine (melting point 110°-112°) with H2O2 ] and 68 g (1 mole) of imidazole is stirred at 110°-115° for 30 minutes. Working up in the customary manner gives 2-chloro-10-[3-(imidazol-1-yl)-propionyl]-phenothiazine-5-oxide, melting point 148°-149°. Hydrochloride, melting point 222°-223°.

Workup

  1. customfor 12 hours

Sources & evidence

ORD record
ord-9ca568d6ef2d4db99a7ab115be2ce2d8
Source dataset
uspto-grants-1981_09
Patent number
US04289768

Reaction notes

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