Cysteamine → Ethyl thiomorpholine-3-carboxylate

HRID 975767

Reaction equation

HRID 975767 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-cd7b7b6a0b964fdc88eeaf84aff66967
Source dataset
uspto-grants-1997_03
Patent number
US05610120

Linked notes

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