Chloral → HCID 13341964, compound

HRID 2286872Notes

Reaction equation

HRID 2286872 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:9]([C:10]([NH2:12])=[O:11])[C:8]([NH2:14])=[CH:7][CH:6]=1)=[O:4].[O:15]=[CH:16][C:17]([Cl:20])([Cl:19])[Cl:18]>COCCOCCOC>[OH:15][CH:16]([NH:12][C:10](=[O:11])[C:9]1[C:8](=[CH:7][CH:6]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:13]=1)[NH2:14])[C:17]([Cl:20])([Cl:19])[Cl:18]

Participants

4

Reactant 2

HCID 6407ChloralHCID 1334196363746-27-0

Product 1

HCID 13341964HCID 13341964, compound

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

5-Methoxycarbonylanthranilamide (1.0 g.) anhydrous chloral (5 ml.) and bis(2-methoxyethyl) ether (20 ml.) were heated together on a steam bath for 20 minutes, then evaporated to dryness under reduced pressure. The residue solidified on stirring with diethyl ether, and it was filtered off and purified by chromatography on silica gel (250 g.). The column was eluted with a mixture of ethyl formate and toluene (7:3 by volume), and 50 ml. fractions were collected. Fractions 10 to 13 were combined and evaporated to dryness, and the residue solidified on stirring with petroleum ether (b.p. 60°-80° C.) to give the required starting material, N-(1-hydroxy-2,2,2-trichloroethyl)-5-methoxycarbonylanthranilamide, m.p. 93° C. (with decomposition).

Workup

  1. customevaporated to dryness under reduced pressure
  2. filtrationwas filtered off
  3. custompurified by chromatography on silica gel (250 g.)
  4. washThe column was eluted with a mixture of ethyl formate and toluene (7:3 by volume), and 50 ml
  5. customfractions were collected
  6. customevaporated to dryness
  7. stirringthe residue solidified on stirring with petroleum ether (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-cadc9b107e524ba5bc664a4f492372d9
Source dataset
uspto-grants-1981_05
Patent number
US04268510

Reaction notes

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