Cysteamine → HCID 18915883, compound

HRID 1379624Notes

Reaction equation

HRID 1379624 reaction equation
[NH2:1][CH2:2][CH2:3][SH:4].C(N(CC)CC)C.Cl[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].Cl[C:20]([O:22][CH2:23][CH3:24])=[O:21]>C(O)C>[CH2:23]([O:22][C:20]([NH:1][CH2:2][CH2:3][S:4][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:21])[CH3:24]

Participants

6

Reactant 4

HCID 6058CysteamineHCID 7751Ethyl chloroacetateHCID 8471Triethylamine2×HCID 10928Ethyl chloroformate

Product 1

HCID 18915883HCID 18915883, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

There was suspended 50 g (0.65 mol) of 2-aminoethanethiol in 660 ml of ethanol and, under cooling with ice, added 65.6 g (0.65 mol) of triethylamine and added dropwise 79.6 g (0.65 mol) of ethyl chloroacetate, and then the mixture was stirred for 1 hour under cooling with ice. Then thereto was added 65.6 g (0.65 mol) of triethylamine and added dropwise 70.6 g (0.65 mol) of ethyl chloroformate, and the mixture was stirred for 1 hour under cooling with ice, and further for hours at room temperature. After the solvent was removed under reduced pressure, the residue was dissolved in chloroform and washed with water, and dried over anhydrous sodium sulfate. Then the solvent was removed under reduced pressure to give 137 g of the titled compound as oily matter.

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. stirringthe mixture was stirred for 1 hour
  4. temperatureunder cooling with ice
  5. waitfurther for hours at room temperature
  6. customAfter the solvent was removed under reduced pressure
  7. dissolutionthe residue was dissolved in chloroform
  8. washwashed with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThen the solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-be88a491ee3d4290bab2aefbe4aadb51
Source dataset
uspto-grants-1997_09
Patent number
US05672597

Reaction notes

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