Thiophosgene → 4-Ethoxycarbonyl-1-piperazinylthiocarbonyl chloride

HRID 1462178Notes

Reaction equation

HRID 1462178 reaction equation
[C:1]([Cl:4])(Cl)=[S:2].[CH2:5]([O:7][C:8]([N:10]1[CH2:15][CH2:14][N:13]([Si](C)(C)C)[CH2:12][CH2:11]1)=[O:9])[CH3:6]>C(OCC)C>[CH2:5]([O:7][C:8]([N:10]1[CH2:11][CH2:12][N:13]([C:1]([Cl:4])=[S:2])[CH2:14][CH2:15]1)=[O:9])[CH3:6]

Participants

4

Reactant 2

HCID 10040ThiophosgeneHCID 133449251-Ethoxycarbonyl-4-trimethylsilylpiperazine

Product 1

HCID 133449264-Ethoxycarbonyl-1-piperazinylthiocarbonyl chloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 4.66 ml of 85% thiophosgene in 200 ml of ethyl ether, cooled to -76° was added, while stirring and under nitrogen, a solution of 7 g of 1-ethoxycarbonyl-4-trimethylsilylpiperazine in 35 ml of ethyl ether over a period of 20 minutes. The mixture was allowed to warm up to room temperature overnight. The suspension was filtered and the filtrate was evaporated to dryness. The residue was crystallized from methylene chloride-hexane to give 4-ethoxycarbonyl-1-piperazinylthiocarbonyl chloride, m.p. 107°-111°.

Workup

  1. additionwas added
  2. filtrationThe suspension was filtered
  3. customthe filtrate was evaporated to dryness
  4. customThe residue was crystallized from methylene chloride-hexane

Sources & evidence

ORD record
ord-fe6291f0ed084cbaa0f5beb555bdd31f
Source dataset
uspto-grants-1984_07
Patent number
US04459232

Reaction notes

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