Hydrochloric Acid → HCID 12046211, compound

16.50 g of sodium hydride with 64% purity and 350 ml of dry dimethyl sulfoxide were supplied to a well dried 1-litre 4-necked flask. Then 101.30 g of ethyl 3,4-dichlorophenylacetate obtained in Example 6 was added dropwise, the solution being stirred at room temperature even after the end of the dropwise addition. Thereafter, 48.61 g of sodium chloroacetate was added and the solution was further stirred at room temperature. At this point, the reaction solution changed from a yellow to a red suspension. The reaction solution was stirred overnight at room temperature, then poured into a mixture of 500 ml of 1N hydrochloric acid and 300 ml of ice water, and stirred vigorously. The reaction mixture was extracted with 800 ml of ether and the organic layer was washed with 500 ml of water (three times) and 500 ml of a saturated saline solution (once). This organic layer was then dried over approximately 50 g of anhydrous sodium sulfate, concentrated to approximately 50 ml solvent and crystallized by treating it with approximately 300 ml of an ether/hexane mixed solvent. The precipitated crystals were filtered out and dried to give 106.07 g of primary crystals of the title substance. Meanwhile, the filtrate was concentrated to produce an oily substance, and it was crystallized by adding 20 ml of ether and 60 ml of hexane. Further, after additional supply of hexane, the precipitated crystals were filtered out and dried to obtain 3.09 g of the secondary crystals (109.16 g when combined with the primary crystals, yield 84.0%) of the title substance.

1. additioneven after the end of the dropwise addition
2. stirringthe solution was further stirred at room temperature
3. stirringThe reaction solution was stirred overnight at room temperature
4. stirringstirred vigorously
5. extractionThe reaction mixture was extracted with 800 ml of ether
6. washthe organic layer was washed with 500 ml of water (three times) and 500 ml of a saturated saline solution (once)
7. dry with materialThis organic layer was then dried over approximately 50 g of anhydrous sodium sulfate
8. concentrationconcentrated to approximately 50 ml solvent
9. customcrystallized
10. additionby treating it with approximately 300 ml of an ether/hexane mixed solvent
11. filtrationThe precipitated crystals were filtered out
12. customdried

ORD record

ord-caeb27d8898b45679d0c1f8e8e80c11e

Source dataset

uspto-grants-2002_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06433174B1