4-Toluenesulfonyl chloride → HCID 53755730, compound

HRID 2255956Notes

Reaction equation

HRID 2255956 reaction equation
[OH:1]/[N:2]=[C:3]1\[CH2:4][CH2:5][CH2:6][C:7]2[O:11][CH:10]=[C:9]([C:12]([OH:14])=[O:13])[C:8]\1=2.[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>N1C=CC=CC=1.Cl>[CH3:25][C:15]1[CH:20]=[CH:19][C:18]([S:21]([O:1][N:2]=[C:3]2[C:8]3[C:9]([C:12]([OH:14])=[O:13])=[CH:10][O:11][C:7]=3[CH2:6][CH2:5][CH2:4]2)(=[O:23])=[O:22])=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 45089073HCID 45089073, compound

Product 1

HCID 53755730HCID 53755730, compoundYield 95.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 1049PyridineSolvent

Procedure

To a partial solution of 2.8 g of (E)-4,5,6,7-tetrahydro-4-(hydroxyimino)-3-benzofurancarboxylic acid in 7 ml of pyridine is added portionwise at 0° C., 3.01 g of p-toluene sulfonyl chloride under argon. The mixture is stirred for 1 hour then diluted with 40 ml of cold 1N HCl, filtered, washed with water and dried with Na2SO4. The filtrate is concentrated in vacuo to give 4.78 g of the desired product as an off-white solid, m.p. 155°-165° C.

Workup

  1. filtrationfiltered
  2. washwashed with water
  3. dry with materialdried with Na2SO4
  4. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-ee677b760d3442bf932d90e6d1b3a04c
Source dataset
uspto-grants-1997_08
Patent number
US05654297

Reaction notes

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