Thiophosgene → 4-Ethoxycarbonyl-1-piperazinylthiocarbonyl chloride

HRID 1462334Notes

Reaction equation

HRID 1462334 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-74158b3790fc4545a26d3fce5ab905f5
Source dataset
uspto-grants-1984_07
Patent number
US04460508

Reaction notes

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