Tetrahydrofuran → HCID 17760233, compound

Temperature

-30 °C

In a 500 mL, three-necked, round-bottomed flask fitted with a mechanical stirrer, nitrogen inlet and thermometer were placed 10 g of 3-methyl-4-nitrobenzoic acid, 200 mL of tetrahydrofuran and 38 mL triethylamine were added to The resulting well-stirred mixture was cooled to -30° C. and 4.7 mL of methane sulfonyl chloride were added dropwise keeping the reaction temperature at -30° C. The resulting suspension was stirred at -30° C. during 30 minutes, after which 8.1 g of 3-amino-3-methyl-1-pentyne hydrochloride were added slowly over a 20 minute period. After the addition was complete the reaction mixture was stirred at -30° C. for an additional 30 minutes. The reaction mixture was then poured into a mixture of 400 mL water and 200 mL of ethyl acetate. The phases were separated and the aqueous layer was extracted with ethyl acetate (2×150 mL). The combined organic phases were washed sequentially with water (1×200 mL), 5% aqueous hydrochloric acid (2×200 mL), water (1×200 mL), 5% aqueous sodium hydroxide (2×200 mL) and finally with water (1×200 mL) and then dried over anhydrous magnesium sulfate. The solvent was removed using a rotary evaporator, yielding the crude product. The crude product was dissolved in 100 mL of methylene chloride and filtered through a small silica gel column yielding 4.11 g of N-(3-methylpent-1-yn-3-yl)-3-methyl-4-nitrobenzamide.

1. customIn a 500 mL, three-necked, round-bottomed flask fitted with a mechanical stirrer, nitrogen inlet
2. additionwere added to The resulting
3. customat -30° C
4. stirringThe resulting suspension was stirred at -30° C. during 30 minutes
5. additionAfter the addition
6. stirringwas stirred at -30° C. for an additional 30 minutes
7. customThe phases were separated
8. extractionthe aqueous layer was extracted with ethyl acetate (2×150 mL)
9. washThe combined organic phases were washed sequentially with water (1×200 mL), 5% aqueous hydrochloric acid (2×200 mL), water (1×200 mL), 5% aqueous sodium hydroxide (2×200 mL) and finally with water (1×200 mL)
10. dry with materialdried over anhydrous magnesium sulfate
11. customThe solvent was removed
12. customa rotary evaporator
13. customyielding the crude product
14. filtrationfiltered through a small silica gel column

ORD record

ord-04ce108b459f41edab6719ca01391419

Source dataset

uspto-grants-1999_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05929098