Toluene → HCID 86739128, compound

HRID 1649558Notes

Reaction equation

HRID 1649558 reaction equation
C(N(CC)CC)C.Cl[C:9]([N:11]([CH:21]=[C:22]=[O:23])[O:12][C:13]1[CH:14]=[N:15][N:16]([CH:18]([CH3:20])[CH3:19])[CH:17]=1)=O.C1([SH:30])C=CC=CC=1.[C:31]1(C)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>>[C:31]1([C:9]([N:11]([CH:21]=[C:22]=[O:23])[O:12][C:13]2[CH:14]=[N:15][N:16]([CH:18]([CH3:20])[CH3:19])[CH:17]=2)=[S:30])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 4

HCID 1140TolueneHCID 7969ThiophenolHCID 8471TriethylamineHCID 86739129HCID 86739129, compound

Product 1

HCID 86739128HCID 86739128, compoundYield 94%

Procedure

g (0.04 mol) of triethylamine were added dropwise to a solution of 9.8 g (0.04 mol) of N-chlorocarbonyl-N-[1-iso-propyl-pyrazol-4-yl-oxy]-carbonyl-methylamine--which had been prepared analogously to Example 2--and 4.4 g (0.04 mol) of thiophenol in 100 ml of toluene. The mixture was subsequently stirred at room temperature for 4 hours and was then extracted twice by shaking with 25 ml of water each time. The organic phase was dried over sodium sulphate and evaporated in vacuo. The residue was subjected to incipient distillation under a high vacuum. 12 g (94% of theory) of N-phenylthiocarbonyl-N-[1-isopropyl-pyrazol-4-yl-oxy]-carbonyl-methylamine were thus obtained as a brown oil with a refractive index nD20 of 1.5662.

Workup

  1. customwhich had been prepared analogously to Example 2
  2. extractionwas then extracted twice
  3. stirringby shaking with 25 ml of water each time
  4. dry with materialThe organic phase was dried over sodium sulphate
  5. customevaporated in vacuo
  6. distillationThe residue was subjected to incipient distillation under a high vacuum

Sources & evidence

ORD record
ord-733691e9adda4b8bbb2935bdc0bd489a
Source dataset
uspto-grants-1983_11
Patent number
US04418073

Reaction notes

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