Hydrogen Sulfide → HCID 86738934, compound

HRID 371441Notes

Reaction equation

HRID 371441 reaction equation
CN(C)C=O.[CH3:6][C:7]1([CH3:34])[C@H:9]([CH2:10][C:11]([Cl:14])([Cl:13])[Cl:12])[C@@H:8]1[C:15]([O:17][CH:18]([C:32]#[N:33])[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:20]=1)=[O:16].N(CCO)(CCO)CCO.[SH2:45]>O>[CH3:6][C:7]1([CH3:34])[C@H:9]([CH2:10][C:11]([Cl:14])([Cl:13])[Cl:12])[C@@H:8]1[C:15]([O:17][CH:18]([C:32](=[S:45])[NH2:33])[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:20]=1)=[O:16]

Participants

6

Reactant 4

HCID 402Hydrogen SulfideHCID 6228DimethylformamideHCID 7618TriethanolamineHCID 86738244HCID 86738244, compound

Product 1

HCID 86738934HCID 86738934, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into 20 ml of N,N-dimethylformamide were dissolved 2.50 g of 3-phenoxy-α-cyanobenzyl cis-2,2-dimethyl-3-(2,2,2-trichloroethyl)cyclopropanecarboxylate and 1 ml of triethanolamine, and hydrogen sulfide gas was bubbled into the solution at room temperature over a period of 15 hours. The resultant reaction mixture was poured into 500 ml of water and extracted with diethyl ether. The ethereal layer was washed with water, dried over anhydrous magnesium sulfate and distilled to remove diethyl ether. By the above procedure there were obtained 2.63 g of 3-phenoxy-α-thiocarbamoylbenzyl cis-2,2-dimethyl-3-(2,2,2-trichloroethyl)cyclopropanecarboxylate [Compound (27)] having the NMR spectrum shown hereinbelow (yield: 98%)

Workup

  1. customwas bubbled into the solution at room temperature over a period of 15 hours
  2. customThe resultant reaction mixture
  3. extractionextracted with diethyl ether
  4. washThe ethereal layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationdistilled
  7. customto remove diethyl ether

Sources & evidence

ORD record
ord-2499cbcb3958411c9ac4853207b2db83
Source dataset
uspto-grants-1985_07
Patent number
US04532258

Reaction notes

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