N,N-Dimethylaminophosphoryl dichloride → HCID 58056279, compound

N,N-Dimethylphosphoramidodichloridate (1.8 mL, 15.22 mmol) was added to a solution of 3-methoxy-4-nitrobenzoic acid (300 mg, 1.52 mmol) in anhydrous 1,2-dimethoxyethane (15 mL) and the resulting mixture was heated at reflux for 110 hours ca. The reaction mixture was then cooled and poured into ice-water (50 mL); the resulting mixture was extracted with diethyl ether (50 mL), the organic layer was separated and the aqueous layer was extracted with dichloromethane (50 mL). The combined organic extracts were concentrated under reduced pressure; the residue was dissolved in dichloromethane and washed with water (30 mL), dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The tan liquid residue was purified by flash chromatography (DCM/MeOH, 98/2) to give 185 mg of 3-methoxy-N,N-dimethyl-4-nitro-benzamide as a yellow oil.

1. temperaturethe resulting mixture was heated
2. temperatureat reflux for 110 hours
3. temperaturewas then cooled
4. extractionthe resulting mixture was extracted with diethyl ether (50 mL)
5. customthe organic layer was separated
6. extractionthe aqueous layer was extracted with dichloromethane (50 mL)
7. concentrationThe combined organic extracts were concentrated under reduced pressure
8. dissolutionthe residue was dissolved in dichloromethane
9. washwashed with water (30 mL)
10. dry with materialdried over anhydrous sodium sulfate
11. filtrationfiltered
12. customevaporated under reduced pressure
13. customThe tan liquid residue was purified by flash chromatography (DCM/MeOH, 98/2)

ORD record

ord-bf7c7ef52e79418998e0a323c7d6afd4

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09255110B2