Phosphorus oxychloride → HCID 21280634, compound

HRID 414441Notes

Reaction equation

P(Cl)(Cl)(Cl)=O.[CH3:6][N:7]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH2:23][CH2:24][CH3:25])=[O:20])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:26]([O-])(=[O:28])C.[Na+]>CN(C)C=O>[CH3:6][N:7]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH2:23][CH2:24][CH3:25])=[O:20])[C:8]1[CH:13]=[CH:12][C:11]([CH:26]=[O:28])=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Phosphorus oxychloride (18.4 g, 0.12 mol) was added dropwise with stirring, at 5° C., under nitrogen, to N,N-dimethylformamide (DMF, 50 mL). The resulting orange solution was stirred for 2 hours, then 27.6 g (0.81 mol) of butyl 6-(N-methyl-N-phenylamino)hexanoate was dropwise. The reaction mixture was stirred at 5° C. for 1 hour and then was heated in a water bath to 90° C., for 4 hours. After cooling the hot solution was poured over 200 g of crushed ice and naturalized to pH 6 by a slow addition of solid sodium acetate with vigorous stirring. The mixture was extracted with three portions of 200 mL dichloromethane. The combined organic extracts were washed three times with water, dried over magnesium sulfate, and the solvent was removed under reduced pressure. The residue was distilled in vacuo yielding 23.4 g (76.8%) of pale yellow oil bp 151°-153° C. (3×10-4 mm).

Workup

stirringThe reaction mixture was stirred at 5° C. for 1 hour
temperatureAfter cooling the hot solution
extractionThe mixture was extracted with three portions of 200 mL dichloromethane
washThe combined organic extracts were washed three times with water
dry with materialdried over magnesium sulfate
customthe solvent was removed under reduced pressure
distillationThe residue was distilled in vacuo

Sources & evidence

ORD record: ord-2d7daccfa28049848c09aaa1928b5e53
Source dataset: uspto-grants-1988_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04792208

Reaction notes

Loading…