2-Pyrrolidone → HCID 12799391, compound

HRID 267913Notes

Reaction equation

HRID 267913 reaction equation
[Cl:1][C:2]1[C:15]2[S:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[NH:16]1[CH2:20][CH2:19][CH2:18][C:17]1=O.P(Cl)(Cl)(Cl)=O>ClCCCl>[Cl:1][C:2]1[C:15]2[S:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]([C:17]3[N:16]([C:17]4[CH2:18][CH2:19][CH2:20][N:16]=4)[CH2:20][CH2:19][CH:18]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 120252-PyrrolidoneHCID 24813Phosphorus oxychlorideHCID 45215204-Chlorophenothiazine

Product 1

HCID 12799391HCID 12799391, compoundYield 17.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

A solution of 4-chlorophenothiazine (32.3 g., 0.134 mole) and 2-pyrrolidinone (23 g., 0.27 mole) in 125 ml. of 1,2-dichloroethane is added dropwise to a solution of phosphorus oxychloride (20.5 g., 0.134 mole) in 50 ml. of 1,2-dichloroethane in about 35 min. Isolation of the product from the reaction mixture according to the procedure of Example 1 provides 7.5 g., (17.1% yield) of 4-CHLORO-10-[1-(1-PYRROLIN-2YL)-2-PYRROLIN-2-YL]PHENOTHIAZINE free base, m.p. 195°-197° C. Analytically pure 4-CHLORO-10-[1(1-PYRROLIN-2-YL)-2PYRROLIN-2-YL]PHENOTHIAZINE HYDROCHLORIDE obtained by crystallization from ethanol-ether has a melting point of 232°-234° C. (corr.). Analysis. Calcd. for C20H18ClN3S.HCl (percent): C, 59.41; H, 4.74; N, 10.39; Cl, 17.53. Found (percent): C, 59.20; H, 4.74; N, 10.59; Cl, 17.46.

Workup

  1. customprovides 7.5 g

Sources & evidence

ORD record
ord-eb1a69f9a15d4b36a001ca90903a1b6c
Source dataset
uspto-grants-1976_03
Patent number
US03946004

Reaction notes

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