Carbonyl Sulfide → HCID 22806790, compound

HRID 1390271Notes

Reaction equation

HRID 1390271 reaction equation
[ClH:1].[CH2:2]([NH:4][C:5](=[O:15])[C@H:6]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[NH2:7])[CH3:3].[C:16](=[S:18])=O>C(Cl)(Cl)Cl>[CH2:2]([NH:4][C:5](=[O:15])[C@H:6]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[NH:7][C:16]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:1])=[CH:11][CH:10]=1)=[S:18])[CH3:3]

Participants

4

Reactant 2

HCID 10039Carbonyl SulfideHCID 70184120HCID 70184120, compound

Product 1

HCID 22806790HCID 22806790, compoundYield 151.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

3.4 G (0.015 mol) of L-phenylalanine ethylamide hydrochloride was added to 80 ml of chloroform. To the mixture was added 3.3 ml (0.03 mol) of N-methylmorphorine while cooling with ice. To the solution was dropwise added 20 ml of chloroform solution containing 0.9 g (0.015 mol) of carbonyl sulfide at a temperature of from 5°to 10° C. in 20 minutes. After stirred for 30 minutes at the same temperature, 30 ml of chloroform solution containing 2.4 g (0.015 mol) of 4-chlorobenzychloride was dropwise added to the solution in 30 minutes. After this, the solution was stirred at room temperature for 1 hour. The solid material obtained in a similar manner to that described in Example 2 was recrystallized from 50 ml of ethylacetate and 50 ml of n-hexane to give 4.1 g of white crystals.

Workup

  1. additionTo the mixture was added 3.3 ml (0.03 mol) of N-methylmorphorine
  2. temperaturewhile cooling with ice
  3. additioncontaining 2.4 g (0.015 mol)
  4. additionof 4-chlorobenzychloride was dropwise added to the solution in 30 minutes
  5. customThe solid material obtained in a similar manner to that
  6. customwas recrystallized from 50 ml of ethylacetate and 50 ml of n-hexane

Sources & evidence

ORD record
ord-584fbb226a35436999d7f65c5da6607a
Source dataset
uspto-grants-1979_02
Patent number
US04138485

Reaction notes

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