Phosphorus oxychloride → 3-(4-(N-(2-ethylhexyl)-N-propylamino)phenyl)-4-cyano-5-dicyanomethylidene-2-oxo-2,5-dihydropyrrole

HRID 361274Notes

Reaction equation

[Na][Na].[C:3]([C:5]1[C:9](=[C:10]([C:13]#[N:14])[C:11]#[N:12])[NH:8][C:7](=[O:15])[C:6]=1O)#[N:4].[CH2:17]([CH:19]([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:20][N:21]([CH2:28][CH2:29][CH3:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH3:18].P(Cl)(Cl)(Cl)=O>CC(C)=O.O.CN(C)C=O>[CH2:17]([CH:19]([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:20][N:21]([C:22]1[CH:23]=[CH:24][C:25]([C:6]2[C:7](=[O:15])[NH:8][C:9](=[C:10]([C:13]#[N:14])[C:11]#[N:12])[C:5]=2[C:3]#[N:4])=[CH:26][CH:27]=1)[CH2:28][CH2:29][CH3:30])[CH3:18]

Participants

Conditions

Temperature: -10 °C

Procedure

A stirred mixture of disodium salt of 4-cyano-5-dicyanomethylidene-3-hydroxy-2-oxo-2,5-dihydropyrrole (29.9 parts) and dry N,N-dimethylformamide (150 parts) was cooled to -10° C. and N-(2-ethylhexyl)-N-propylaniline containing 30% acetic anhydride (63 parts) was added followed by the dropwise addition of phosphorous oxychloride (34 parts) maintaining the temperature at less than -5° C. The mixture was allowed to warm up to room temperature and stirred for 20 hours. The reaction mixture was poured into a stirred mixture of ice and water (200 parts) and acetone (200 parts) and then stirred for 0.5 hours. The solid was filtered off, washed with hot water and dried under vacuum to give 3-(4-(N-(2-ethylhexyl)-N-propylamino)phenyl)-4-cyano-5-dicyanomethylidene-2-oxo-2,5-dihydropyrrole (48.5 parts, 90%).

Workup

temperaturemaintaining the temperature at less than -5° C
temperatureto warm up to room temperature
stirringstirred for 0.5 hours
filtrationThe solid was filtered off
washwashed with hot water
customdried under vacuum

Sources & evidence

ORD record: ord-943de0dbe3604bcc9576cca7d6661385
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05865857

Reaction notes

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