Triethylamine → N-(2-difluoromethoxybenzenesulfonyl)-imidocarbonic acid diethyl ester

HRID 1249255Notes

Reaction equation

HRID 1249255 reaction equation
C(N(CC)CC)C.[F:8][CH:9]([F:21])[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:17](Cl)(=[O:19])=[O:18].[CH2:22]([O:24][C:25](=[NH:29])[O:26][CH2:27][CH3:28])[CH3:23]>CC(C)=O>[CH2:22]([O:24][C:25](=[N:29][S:17]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[O:10][CH:9]([F:21])[F:8])(=[O:19])=[O:18])[O:26][CH2:27][CH3:28])[CH3:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76054Diethyl imidocarbonateHCID 137294512-(Difluoromethoxy)benzene-1-sulfonyl chloride

Product 1

HCID 54050282N-(2-difluoromethoxybenzenesulfonyl)-imidocarbonic acid diethyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

11.1 g (0.11 mol) of triethylamine are added dropwise at room temperature, with stirring, to a solution of 24.3 g (0.1 mol) of 2-difluoromethoxy-benzenesulfonyl chloride and 11.7 g (0.1 mol) of imidocarbonic acid diethyl ester in 70 ml of acetone. The reaction proceeds slightly exothermically. The reaction mixture is stirred for some hours at room temperature, and the triethylamine hydrochloride is then filtered off. The mother liquor is concentrated by evaporation, and the oil remaining is chromatographed by means of chloroform/ether/petroleum ether (3:3:2) on a silica gel column. After the eluate has been evaporated, there remain 23 g of the above ester, which crystallise (72% of theory), m.p. 80°-81° C.

Workup

  1. filtrationthe triethylamine hydrochloride is then filtered off
  2. concentrationThe mother liquor is concentrated by evaporation
  3. customthe oil remaining is chromatographed by means of chloroform/ether/petroleum ether (3:3:2) on a silica gel column
  4. customAfter the eluate has been evaporated
  5. customcrystallise (72% of theory), m.p. 80°-81° C.

Sources & evidence

ORD record
ord-b00052dcb3d24a559654e46d322dc00b
Source dataset
uspto-grants-1986_12
Patent number
US04629802

Reaction notes

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