Cysteamine → Ethyl thiomorpholine-3-carboxylate

HRID 1489868Notes

Reaction equation

HRID 1489868 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-36eb227f8e72466e9780aa7ee37534a9
Source dataset
uspto-grants-1997_10
Patent number
US05679791

Reaction notes

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