Water → HCID 20688322, compound

Temperature

10 °C

Taurine (50 g, 0.40 mol) and sodium carbonate (48 g, 0.45 mol) were combined with 250 mL of water in a 1-L flask and chilled in an ice bath (10° C.). Bromoacetyl bromide (100 g, 0.50 mol) in 250 mL of methylene chloride was added dropwise over a 1 hr period with rapid stirring while maintaining the temperature at 10°-15° C. After addition, the ice bath was removed and the mixture was stirred for 3 hr. The aqueous layer was separated and washed with two portions of methylene chloride, and most of the water was evaporated affording a moist white solid. The solid was washed thoroughly with acetone and dried (90 g, 85% yield). The product was purified by dissolving it in 1200 mL of hot methanol, filtering, and evaporating the methanol until the product crystallized out (volume ca 650 mL). This afforded 47 g (44% yield) of product; mp>250° C. Anal. Calcd. for C4H7BrNO4SNa: C, 17.9; H, 2.6; N, 5.4. Found: C, 17.6; H, 2.4; N, 4.5.

1. temperaturewhile maintaining the temperature at 10°-15° C
2. additionAfter addition
3. customthe ice bath was removed
4. stirringthe mixture was stirred for 3 hr
5. customThe aqueous layer was separated
6. washwashed with two portions of methylene chloride
7. custommost of the water was evaporated
8. customaffording a moist white solid
9. washThe solid was washed thoroughly with acetone
10. customdried (90 g, 85% yield)
11. customThe product was purified
12. dissolutionby dissolving it in 1200 mL of hot methanol
13. filtrationfiltering
14. customevaporating the methanol until the product
15. customcrystallized out (volume ca 650 mL)

ORD record

ord-b10b4406506f4fe9971e0545fbc207eb

Source dataset

uspto-grants-1992_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05091298