p-Toluenesulphonyl cyanide → HCID 19898984, compound

HRID 1196618Notes

Reaction equation

HRID 1196618 reaction equation
[C:1]1([CH3:12])[CH:6]=[CH:5][C:4]([S:7]([C:10]#[N:11])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[Cl:13][C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[C:16]([Cl:21])[C:15]=1[NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]1OC(=O)[S:31][N:30]=1>ClC1C=CC=C(Cl)C=1>[Cl:13][C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[C:16]([Cl:21])[C:15]=1[NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]1[N:11]=[C:10]([S:7]([C:4]2[CH:3]=[CH:2][C:1]([CH3:12])=[CH:6][CH:5]=2)(=[O:8])=[O:9])[S:31][N:30]=1

Participants

4

Reactant 2

HCID 87946p-Toluenesulphonyl cyanideHCID 19898987HCID 19898987, compound

Product 1

HCID 19898984HCID 19898984, compound

Reagents, catalysts & solvents 1

HCID 109431,3-DichlorobenzeneSolvent

Procedure

To a 155° C. solution of p-toluenesulfonyl cyanide (420 mg, 2.32 mmols) in 5 mL of m-dichlorobenzene is added 5-[2 [(2,6-dichloro-3-methylphenyl]amino]phenyl]-1,3,4-oxathiazol-2-one (442 mg, 1.25 mmols) in three portions. Heating is continued for 1.5 hours. The solution is cooled to room temperature and directly purified by flash chromatography, eluting with 10:1 hexane:diethyl ether providing 446 mg (73%) of 2,6-dichloro-3-methyl-N-[2-[5-[(4-methylphenyl)sulfonyl]-1,2,4-thiadiazol-3-yl]phenyl]benzenamide as a bright yellow solid; mp 130.5°-135° C.

Workup

  1. temperatureHeating
  2. customdirectly purified by flash chromatography
  3. washeluting with 10:1 hexane

Sources & evidence

ORD record
ord-77fac7b026f1422d92c832dca6a6d325
Source dataset
uspto-grants-1992_05
Patent number
US05114958

Reaction notes

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