Triethylamine → HCID 20344122, compound

HRID 2049641Notes

Reaction equation

HRID 2049641 reaction equation
[Cl:1][C:2]([Cl:6])([Cl:5])[S:3]Cl.C(N(CC)CC)C.[NH:14]1[CH2:20][C:18](=[O:19])[NH:17][C:15]1=[O:16]>C(OCC)(=O)C>[Cl:1][C:2]([Cl:6])([Cl:5])[S:3][N:14]1[CH2:20][C:18](=[O:19])[N:17]([S:3][C:2]([Cl:6])([Cl:5])[Cl:1])[C:15]1=[O:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10006HydantoinHCID 11666Trichloromethanesulfenyl chloride

Product 1

HCID 20344122HCID 20344122, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

At about 0° C., 37.2 g (0.2 mole) of trichloromethylsulfenyl chloride and subsequently 20.2 g (0.2 mole) of triethylamine are dripped, while stirring thoroughly, into a suspension of 10 g (0.1 mole) of hydantoin in 150 ml of anhydrous ethyl acetate. After stirring for 90 minutes at room temperature, the precipitated triethylamine hydrochloride is filtered off and washed with 100 ml of ethyl acetate. The filtrate is concentrated and the residue is crystallized by trituration with n-pentane. There is obtained 36.1 g (90.5% of theory) of 1,3-bis-(trichloromethylthio)-hydantoin; m.p.: 142° C.

Workup

  1. customAt about 0° C.
  2. filtrationthe precipitated triethylamine hydrochloride is filtered off
  3. washwashed with 100 ml of ethyl acetate
  4. concentrationThe filtrate is concentrated
  5. customthe residue is crystallized by trituration with n-pentane

Sources & evidence

ORD record
ord-bf4f3b84abc04be9a1710d509d2d8831
Source dataset
uspto-grants-1980_04
Patent number
US04198423

Reaction notes

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