Cysteamine → Ethyl thiomorpholine-3-carboxylate

HRID 725230

Reaction equation

HRID 725230 reaction equation
[NH2:1][CH2:2][CH2:3][SH:4].C(N(CC)CC)C.Br[CH:13]([CH2:19]Br)[C:14]([O:16][CH2:17][CH3:18])=[O:15].C(Cl)(Cl)Cl.C1(C)C=CC=CC=1>C(Cl)(Cl)Cl>[NH:1]1[CH2:2][CH2:3][S:4][CH2:19][CH:13]1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

6

Reactant 4

HCID 6058CysteamineHCID 8471TriethylamineHCID 97945Ethyl 2,3-dibromopropionateHCID 22987606Toluene trichloromethane

Product 1

HCID 13604869Ethyl thiomorpholine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A warm solution of 2-aminoethanethiol (10.0 g, 0.130 mol) and triethylamine (36 mL, 0.260 mol) in chloroform is added over 5 minutes to a solution of ethyl 2,3-dibromopropionate (33.9 g, 0.130 mol) in a chloroform/toluene (1:1.6) solution. The reaction mixture is stirred at room temperature for 2.5 hours, filtered and concentrated in vacuo to obtain an orange liquid. The liquid is vacuum distilled to give the title product as a colorless liquid, bp 121°-124° C. at 3 mm Hg.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customto obtain an orange liquid
  4. distillationdistilled

Sources & evidence

ORD record
ord-f812b549d9654a7b9d4c9b4db3c56f9e
Source dataset
uspto-grants-1998_01
Patent number
US05705644

Linked notes

Loading…