Imidazole → HCID 14125903, compound

82.6 g=0.3 mol of 1-bromo-3-chloropropyl 4-methylphenyl ketone were added in portions at 0°-5° C. with stirring and cooling to a solution of 102 g=1.5 mol of imidazole in 150 ml of dimethylformamide, and the mixture was stirred for 15 hours at room temperature. For work-up, the mixture was poured into 1.5 liters of ice water and extracted twice with 150 ml of methylene chloride in each case, and the organic phase was washed twice with 100 ml of 2N NaOH in each case, dried over sodium sulfate and filtered. The solution thus prepared of the corresponding compound of the formula VII was added dropwise at 20° C. with vigorous stirring and cooling to a mixture of 70 ml of 50% strength sodium hydroxide solution and 1.6 g of tetrabutylammonium bromide, and the mixture was stirred for 8 hours at 20° C. and worked up as specified in Example 1. The oily residue (66.5 g, 98% of theory) crystallized. A sample of this had the melting point: 88°-90° C. from methyl tert.butyl ether.

1. stirringthe mixture was stirred for 15 hours at room temperature
2. extractionextracted twice with 150 ml of methylene chloride in each case
3. washthe organic phase was washed twice with 100 ml of 2N NaOH in each case
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. customThe solution thus prepared of the corresponding compound of the formula VII
7. additionwas added dropwise at 20° C.
8. stirringwith vigorous stirring
9. stirringthe mixture was stirred for 8 hours at 20° C.
10. customThe oily residue (66.5 g, 98% of theory) crystallized

ORD record

ord-fa90dfd7a3f74c0c939da9775cd6d147

Source dataset

uspto-grants-1989_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04870088