Dimethoxymethane → HCID 19047125, compound

To 0.976 g (5.02 mmol) of 6-nitro-2H-1,4-benzoxazin-3(4H)-one in 100 ml of chloroform was added 2 ml of dimethoxymethane. Phosphorous pentoxide (5 g, 35 mmol) was added portionwise and the reaction mixture was stirred at room temperature for 16 hours. TLC analyses showed the starting material was still present therefore additional dimethoxymethane (2 ml) was added along with several batches of phosphorous pentoxide (2×1.2 g and 2.0 g) and chloroform (50 ml). The reaction was stirred for an additional 16 hours then cautiously quenched with water (50 ml). The reaction mixture was slowly neutralized with 50 ml of 1N NaOH during which time an exotherm occurred. When the reaction mixture had cooled to room temperature, the layers were separated and the aqueous phase was extracted with chloroform (2×50 ml). The combined organic phases were washed with water (2×50 ml), dried over MgSO4 and concentrated to afford the desired product (0.5 g, 42% yield) as a pale yellow solid.

1. stirringThe reaction was stirred for an additional 16 hours
2. customthen cautiously quenched with water (50 ml)
3. temperatureWhen the reaction mixture had cooled to room temperature
4. customthe layers were separated
5. extractionthe aqueous phase was extracted with chloroform (2×50 ml)
6. washThe combined organic phases were washed with water (2×50 ml)
7. dry with materialdried over MgSO4
8. concentrationconcentrated

ORD record

ord-df7413dd4f9c4b96a423ef824456f8bd

Source dataset

uspto-grants-1993_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05238908