Triethylamine → HCID 178522669, compound

To a mixture of 3-(biphenyl-4-yloxymethyl)benzoic acid (2.36 g, 7.5 mmol, prepared as described in example 20) and 2 drops of N,N'-dimethylformamide in dry tetrahydrofuran (25 ml) was added dropwise thionyl chloride (1.7 ml, 22.5 mmol) and the resulting reaction mixture was stirred at reflux temperature for 3 h. The volatiles were evaporated in vacuo and the solid residue was dissolved in dichloromethane (20 ml) and added dropwise to a stirred suspension of 5-amino-tetrazole monohydrate (0.86 g, 8.3 mmol) and triethylamine (3.2 ml, 22.5 mmol) in dichloromethane (10 ml). After the addition was complete pyridine (5 ml) and 4-dimethylaminopyridine (10 mg) were added and the resuiting mixture was stirred at room temperature for 48 h. The volatiles were evaporated in vacuo and the residue was suspended in water (100 ml) and acidified to pH=3 with concentrated hydrochloric acid. Ethyl acetate (100 ml) was added and the mixture was stirred for 0.5 h. The precipitate was filtered off and washed with water (2×10 ml) and dried in vacuo at 50° C. afforded 1.39 g (50%) of the title compound as a solid.

1. customthe resulting reaction mixture
2. temperatureat reflux temperature for 3 h
3. customThe volatiles were evaporated in vacuo
4. dissolutionthe solid residue was dissolved in dichloromethane (20 ml)
5. additionAfter the addition
6. additionwere added
7. stirringthe resuiting mixture was stirred at room temperature for 48 h
8. customThe volatiles were evaporated in vacuo
9. additionEthyl acetate (100 ml) was added
10. stirringthe mixture was stirred for 0.5 h
11. filtrationThe precipitate was filtered off
12. washwashed with water (2×10 ml)
13. customdried in vacuo at 50° C.

ORD record

ord-12300fe3d6474eff8b5a8fe6e8bdb4c0

Source dataset

uspto-grants-1999_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05972978