Phosphorus oxychloride → 10-(5,5-Dimethyl-1-pyrrolin-2-YL)-2-(trifluoromethyl)phenoxazine

HRID 839373Notes

Reaction equation

HRID 839373 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:16]=[CH:15][C:14]2[O:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][C:5]=2[CH:4]=1.[CH3:19][C:20]1([CH3:26])[NH:24][C:23](=O)[CH2:22][CH2:21]1.P(Cl)(Cl)(Cl)=O>>[CH3:19][C:20]1([CH3:26])[N:24]=[C:23]([N:6]2[C:5]3[CH:4]=[C:3]([C:2]([F:1])([F:17])[F:18])[CH:16]=[CH:15][C:14]=3[O:13][C:12]3[C:7]2=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:22][CH2:21]1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 104673212-TrifluoromethylphenoxazineHCID 111262105,5-dimethylpyrrolidin-2-one

Product 1

HCID 2275426810-(5,5-Dimethyl-1-pyrrolin-2-YL)-2-(trifluoromethyl)phenoxazine

Procedure

Reaction of 2-(trifluoromethyl)phenoxazine, 5,5-dimethyl-2-pyrrolidinone and phosphorus oxychloride according to the procedure of Example 1 provides the free base 10-(5,5-DIMETHYL-1-PYRROLIN-2-YL)-2-(TRIFLUOROMETHYL)PHENOXAZINE, m.p. 64°-67° C. Conversion of the free base to the hydrochloride salt affords 10-(5,5-DIMETHYL-1-PYRROLIN-2-YL)-2-(TRIFLUOROMETHYL)PHENOXAZINE HYDROCHLORIDE, m.p. 204.5°-207.5° C. (dec.) (corr.), in a 30% overall yield.

Sources & evidence

ORD record
ord-79453af4e2a04115821327f69d6b65b7
Source dataset
uspto-grants-1978_06
Patent number
US04094981

Reaction notes

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