Triethylamine → HCID 21489482, compound

HRID 1974356Notes

Reaction equation

HRID 1974356 reaction equation
[F:1][C:2]([Cl:6])([Cl:5])[S:3]Cl.[Cl:7][C:8]1[CH:9]=[C:10]([N:15]2[C:19](=[O:20])[CH:18]([CH3:21])[NH:17][C:16]2=[O:22])[CH:11]=[CH:12][C:13]=1[Cl:14].C(N(CC)CC)C>C(OC(=O)C)C>[Cl:5][C:2]([Cl:6])([F:1])[S:3][N:17]1[CH:18]([CH3:21])[C:19](=[O:20])[N:15]([C:10]2[CH:11]=[CH:12][C:13]([Cl:14])=[C:8]([Cl:7])[CH:9]=2)[C:16]1=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 759261,1-Dichloro-1-fluoromethanesulfenyl chlorideHCID 12900458HCID 12900458, compound

Product 1

HCID 21489482HCID 21489482, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

20.4 g of fluorodichloromethanesulphenyl chloride is added dropwise at 0° C, with thorough stirring, to 25.9 g of 3-(3',4'-dichlorophenyl)-5-methyl-imidazolidine-2,4-dione in 500 ml of acetic acid ethyl ester, and after 2 hours an addition is made dropwise, likewise at 0° C. of 12.1 g of triethylamine in 100 ml of acetic acid ethyl ester. After the whole has been stirred for 3 hours at room temperature, the triethylamine hydrochloride is filtered off; the solvent is evaporated off from the filtrate and the residue is recrystallised in methanol. Compound No. 2 melts at 138° - 140° C after recrystallisation.

Workup

  1. additionafter 2 hours an addition
  2. filtrationthe triethylamine hydrochloride is filtered off
  3. customthe solvent is evaporated off from the filtrate
  4. customthe residue is recrystallised in methanol
  5. custom2 melts at 138° - 140° C after recrystallisation

Sources & evidence

ORD record
ord-2bb2b8fa776f41179e1759c3afea9eb6
Source dataset
uspto-grants-1976_12
Patent number
US04000303

Reaction notes

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