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

HRID 1577825Notes

Reaction equation

HRID 1577825 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]([C:16](=[O:24])[CH2:17][CH2:18][N:19]3[CH:23]=[CH:22][N:21]=[CH:20]3)[C:4]=2[CH:3]=1.O.C([O-])(O)=[O:27].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[S:12](=[O:27])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]([C:16](=[O:24])[CH2:17][CH2:18][N:19]3[CH:23]=[CH:22][N:21]=[CH:20]3)[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 516892Sodium BicarbonateHCID 20569747HCID 20569747, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 14 g of SO2Cl2 in 65 ml of CH2Cl2 is added dropwise over the course of 1 hour and at 10° to a mixture of 35.6 g of 2-chloro-10-[3-(imidazol-1-yl)-propionyl]-phenothiazine, 8.2 g of silica gel, 8.2 ml of water and 850 ml of CH2Cl2. Stirring is continued for 2 hours at 10°; 100 ml of water is added dropwise and the mixture is rendered alkaline by adding NaHCO3. Working up in the customary manner gives 2-chloro-10-[3-(imidazol-1-yl)-propionyl]-phenothiazine-5-oxide, melting point 148°-149°.

Sources & evidence

ORD record
ord-927654b5a45548cba4513922d1da8208
Source dataset
uspto-grants-1981_09
Patent number
US04289768

Reaction notes

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