Phosphorus oxychloride → 2-Chloro-10-(5-methyl-1-pyrrolin-2-YL)phenoxazine

HRID 2163239

Reaction equation

HRID 2163239 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[NH:5][C:4]=2[CH:3]=1.[CH3:16][CH:17]1[NH:21][C:20](=O)[CH2:19][CH2:18]1.P(Cl)(Cl)(Cl)=O>>[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]([C:20]3[CH2:19][CH2:18][CH:17]([CH3:16])[N:21]=3)[C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 660555-Methyl-2-pyrrolidoneHCID 106325802-Chlorophenoxazine

Product 1

HCID 227542622-Chloro-10-(5-methyl-1-pyrrolin-2-YL)phenoxazine

Procedure

Reaction of 2-chlorophenoxazine, 5-methyl-2-pyrrolidinone and phosphorus oxychloride according to the procedure of Example 1 provides the free base 2-CHLORO-10-(5-METHYL-1-PYRROLIN-2-YL)-PHENOXAZINE as a distillable oil, b.p. 150-170° C. at 0.1 mm Hg. Conversion of the free base to the hydrochloride salt affords 2-CHLORO-10-(5-METHYL-1-PYRROLIN-2-YL)PHENOXAZINE HYDROCHLORIDE, m.p. 213.5-215.5° C., as a crystalline solid in a 34% overall yield by refluxing with benzene.

Sources & evidence

ORD record
ord-72071dc0f9514c0d9938464318c97a2a
Source dataset
uspto-grants-1979_01
Patent number
US04132794

Linked notes

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