Cysteamine → Ethyl thiomorpholine-3-carboxylate
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
Product 1
Reagents, catalysts & solvents 1
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
- filtrationfiltered
- concentrationconcentrated in vacuo
- customto obtain an orange liquid
- distillationdistilled
Sources & evidence
- ORD record
- ord-0ea27041f7c3480cb095d9b064085a09
- Source dataset
- uspto-grants-1998_03
- Patent number
- US05726126
Reaction notes
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