4-Toluenesulfonyl chloride → HCID 53828981, compound

HRID 1659895Notes

Reaction equation

HRID 1659895 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[Cl:12][C:13]1[C:14]([Cl:25])=[CH:15][C:16]2[O:21][CH2:20][CH2:19][C:18](=[N:22][OH:23])[C:17]=2[CH:24]=1>N1C=CC=CC=1>[Cl:12][C:13]1[C:14]([Cl:25])=[CH:15][C:16]2[O:21][CH2:20][CH2:19][C:18](=[N:22][O:23][S:7]([C:4]3[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=3)(=[O:9])=[O:8])[C:17]=2[CH:24]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 857730826,7-Dichloro-2,3-dihydro-4H-1-benzopyran-4-one oxime

Product 1

HCID 53828981HCID 53828981, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of p-toluenesulfonyl chloride (103 g) in 125 ml pyridine was added dropwise at 5°-10° to 6,7-dichloro-2,3-dihydro-4-(hydroxyimino)-4H-1-benzopyran (62.5 g) in 250 ml pyridine. The reaction mixture was then stirred for 20 hours at room temperature, poured into ice-water to separate out the title compound, which was filtered, washed several times with water, then once with ether, and finally dried in air. Yield: 101.8 g; m.p. 180°-184°.

Workup

  1. customto separate out the title compound, which
  2. filtrationwas filtered
  3. washwashed several times with water
  4. dry with materialonce with ether, and finally dried in air

Sources & evidence

ORD record
ord-19303a9928b9407aac4fb177cf7d67be
Source dataset
uspto-grants-1981_12
Patent number
US04305954

Reaction notes

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