Thiophosgene → 4-Ethoxycarbonyl-1-piperazinylthiocarbonyl chloride

HRID 1462445Notes

Reaction equation

HRID 1462445 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° is 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 is allowed to warm up to room temperature overnight. The suspension is filtered and the filtrate is evaporated to dryness. The residue is crystallized from methylene chloridehexane to give 4-ethoxycarbonyl-1-piperazinylthiocarbonyl chloride, m.p. 107°-111°.

Workup

  1. additionis added
  2. filtrationThe suspension is filtered
  3. customthe filtrate is evaporated to dryness
  4. customThe residue is crystallized from methylene chloridehexane

Sources & evidence

ORD record
ord-cb570bf3d6be410db649bcca16b3a93c
Source dataset
uspto-grants-1984_07
Patent number
US04460587

Reaction notes

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