Triethylamine → HCID 86738804, compound

HRID 354537Notes

Reaction equation

HRID 354537 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]([C:29]([F:32])([F:31])[F:30])=[CH:10][C@@H:11]1[C@H:13]([C:14]([O:16][CH2:17][C:18]2[C:23]([CH3:24])=[CH:22][CH:21]=[C:20]([NH2:25])[C:19]=2[CH3:26])=[O:15])[C:12]1([CH3:28])[CH3:27].[C:33](Cl)(Cl)=[S:34]>C(Cl)(Cl)Cl>[Cl:8][C:9]([C:29]([F:30])([F:31])[F:32])=[CH:10][C@@H:11]1[C@H:13]([C:14]([O:16][CH2:17][C:18]2[C:23]([CH3:24])=[CH:22][CH:21]=[C:20]([N:25]=[C:33]=[S:34])[C:19]=2[CH3:26])=[O:15])[C:12]1([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 86738802HCID 86738802, compound

Product 1

HCID 86738804HCID 86738804, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Triethylamine (0.5 gram, 0.005 mole) was added to a solution of (3-amino-2,6-dimethylphenyl)methyl cis-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylate (2.03 grams, 0.005 mole) in chloroform (20 ml) and cooled to 0°. Thiophosgene (0.58 gram, 0.005 mole) was added, and the reaction mixture was allowed to come to room temperature. The solvent was evaporated, and the residue was dissolved in diethyl ether. The solution was washed with water, dried over magnesium sulfate and filtered. The solvent was evaporated to give (3-isothiocyanato-2,6-dimethylphenyl)methyl cis-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylate (1.71 grams, mp 60°).

Workup

  1. temperaturecooled to 0°
  2. customto come to room temperature
  3. customThe solvent was evaporated
  4. dissolutionthe residue was dissolved in diethyl ether
  5. washThe solution was washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customThe solvent was evaporated

Sources & evidence

ORD record
ord-817b7a13607b4c40a61d3b570a9ebd3f
Source dataset
uspto-grants-1983_03
Patent number
US04375476

Reaction notes

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