Cysteamine → Ethyl thiomorpholine-3-carboxylate

HRID 1473

Reaction equation

HRID 1473 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-di-bromopropionate (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-0ea27041f7c3480cb095d9b064085a09
Source dataset
uspto-grants-1998_03
Patent number
US05726126

Linked notes

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