(Chlorothio)formyl chloride → HCID 19898987, compound

HRID 1196617Notes

Reaction equation

HRID 1196617 reaction equation
[Cl:1][C:2]1[C:17]([CH3:18])=[CH:16][CH:15]=[C:14]([Cl:19])[C:3]=1[NH:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([NH2:9])=[O:8].Cl[C:21]([S:23]Cl)=[O:22]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:17]([CH3:18])=[CH:16][CH:15]=[C:14]([Cl:19])[C:3]=1[NH:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]1[O:8][C:21](=[O:22])[S:23][N:9]=1

Participants

4

Reactant 2

HCID 75990(Chlorothio)formyl chlorideHCID 14951346HCID 14951346, compound

Product 1

HCID 19898987HCID 19898987, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a 90° C. solution of 2-(2,6-dichloro-3-methylanilino)benzamide (2.300 g, 7.79 mmols) [prepared according to Juby, J. Med. Chem., 11, 111 (1968)] in 40 mL of toluene is added chlorocarbonylsulfenyl chloride (1.300 mL, 15.38 mmols). Heating is continued at 90° C. for 1 hour. The solution is concentrated in vacuo and purified by flash chromatography, eluting with 10:1 hexane:diethyl ether providing 280 mg (10%) of 5-[2-[(2,6-dichloro-3-methylphenyl]amino]phenyl]-1,3,4-oxathiazol-2-one as a white solid; mp 135°-137° C.

Workup

  1. temperatureHeating
  2. concentrationThe solution is concentrated in vacuo
  3. custompurified by flash chromatography
  4. washeluting with 10:1 hexane

Sources & evidence

ORD record
ord-594537faa0d442f8b8dd2f2ac7d5b05b
Source dataset
uspto-grants-1992_05
Patent number
US05114958

Reaction notes

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