Triethylamine → HCID 88770053, compound

HRID 126907Notes

Reaction equation

HRID 126907 reaction equation
C(N(CC)CC)C.F[C:9]([N:11]([CH3:40])[S:12][N:13]([C:15]([O:17][N:18]=[C:19]([CH3:39])[C:20](=[N:22][O:23][C:24]([N:26]([CH3:38])[S:27][N:28]([C:30]([O:32][N:33]=[C:34]([S:36][CH3:37])[CH3:35])=[O:31])[CH3:29])=[O:25])[CH3:21])=[O:16])[CH3:14])=[O:10].[CH3:41][N:42]([CH3:50])[C:43](=[O:49])[C:44]([S:47][CH3:48])=[N:45][OH:46]>C(Cl)Cl>[CH3:39][C:19](=[N:18][O:17][C:15]([N:13]([CH3:14])[S:12][N:11]([C:9]([O:46][N:45]=[C:44]([S:47][CH3:48])[C:43]([N:42]([CH3:50])[CH3:41])=[O:49])=[O:10])[CH3:40])=[O:16])[C:20]([CH3:21])=[N:22][O:23][C:24]([N:26]([CH3:38])[S:27][N:28]([CH3:29])[C:30]([O:32][N:33]=[C:34]([S:36][CH3:37])[CH3:35])=[O:31])=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 54363941HCID 54363941, compoundHCID 59846971Oxamyl oxime

Product 1

HCID 88770053HCID 88770053, compoundYield 13.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1 g of triethylamine in 10 ml of methylene chloride was added dropwise to a solution of 3 g of the crude carbamic fluoride and 1.1 g of methyl 2-(dimethylamino)-N-hydroxy-2-oxoethanimidothioate in 50 ml of methylene chloride at 10° to 20° C. and stirred at room temperature for 2.5 hours. The solution was washed with three 50 ml portions of water, and the organic layer was dried over anhydrous magnesium sulfate. The mixture was filtered, and the filtrate was evaporated. Ether was added to the crude product followed by dilution with methylene chloride until the mass could flow freely. The solid was separated by filtration to give a mixture. The mother liquor was concentrated and diluted with ethers to give 0.5 g of the title compound, m.p. 87°-110° C. (glass).

Workup

  1. washThe solution was washed with three 50 ml portions of water
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated
  5. additionEther was added to the crude product
  6. customThe solid was separated by filtration
  7. customto give a mixture
  8. concentrationThe mother liquor was concentrated
  9. additiondiluted with ethers

Sources & evidence

ORD record
ord-c607b1f5e3a14b6aad21ce43e91f8292
Source dataset
uspto-grants-1981_03
Patent number
US04254141

Reaction notes

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