Triethylamine → N-ethoxycarbonyl-N'-chlorothiocarbonylhexahydropyridazine

HRID 1995851Notes

Reaction equation

HRID 1995851 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH2:9][CH2:8][NH:7]1)=[O:5])[CH3:2].C(N(CC)CC)C.[C:19](Cl)([Cl:21])=[S:20]>C1C=CC=CC=1>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH2:9][CH2:8][N:7]1[C:19]([Cl:21])=[S:20])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 30143771(2H)-Pyridazinecarboxylic acid, tetrahydro-, ethyl ester

Product 1

HCID 53642385N-ethoxycarbonyl-N'-chlorothiocarbonylhexahydropyridazine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent3×

Procedure

With the temperature maintained at 30° or below, a mixture of N-ethoxycarbonylhexahydropyridazine (1.5 g, 9.49 mmol) and triethylamine (1.0 g, 9.49 mmol) in 8 ml of benzene is added dropwise to a stirring solution of thiophosgene (1.1 g, 9.49 mmol) in 10 ml of benzene. The reaction is stirred at RT for 4 hours, and is then diluted with benzene to 50 ml, quickly washed with water and with brine, dried and stripped to give N-ethoxycarbonyl-N'-chlorothiocarbonylhexahydropyridazine.

Workup

  1. temperatureWith the temperature maintained at 30° or below
  2. washquickly washed with water and with brine
  3. customdried

Sources & evidence

ORD record
ord-0454f0475099429ca02a5bac0249db6a
Source dataset
uspto-grants-1983_09
Patent number
US04406689

Reaction notes

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