Triethylamine → Methyl 4-Thiomorpholinobutyrate

HRID 267348Notes

Reaction equation

HRID 267348 reaction equation
I[CH2:2][CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6].C(N(CC)CC)C.[NH:16]1[CH2:21][CH2:20][S:19][CH2:18][CH2:17]1>C1C=CC=CC=1>[S:19]1[CH2:20][CH2:21][N:16]([CH2:2][CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6])[CH2:17][CH2:18]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67164ThiomorpholineHCID 547991Methyl 4-iodobutanoate

Product 1

HCID 21555513Methyl 4-Thiomorpholinobutyrate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 64.0 g. (0.28 mole) of methyl γ-iodobutyrate, 28.0 g. (0.28 mole) of triethylamine, 28.7 g. (0.28 mole) of thiomorpholine (J. Am. Chem. Soc. 76, 1187 (1954)) and 1 liter of benzene was stirred and heated at 60°-70°C. for 18 hours. After cooling the reaction mixture, the precipitated amine hydroiodide was removed by suction filtration. The benzene solution was evaporated to give a orange-red residue which was vacuum distilled (b.p. 84°-85°C. at 0.1 mm) to give 28.38 g. (50%) of the product as a colorless liquid.

Workup

  1. additionA mixture of 64.0 g
  2. temperatureheated at 60°-70°C. for 18 hours
  3. temperatureAfter cooling the reaction mixture
  4. customthe precipitated amine hydroiodide was removed by suction filtration
  5. customThe benzene solution was evaporated
  6. customto give a orange-red residue which
  7. distillationdistilled (b.p. 84°-85°C. at 0.1 mm)
  8. customto give 28.38 g

Sources & evidence

ORD record
ord-92fd8cf768564b8da6fee7442a9d1203
Source dataset
uspto-grants-1976_03
Patent number
US03941782

Reaction notes

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