4-Toluenesulfonyl chloride → HCID 53697721, compound

HRID 1389713Notes

Reaction equation

HRID 1389713 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:23])[CH2:9][C:10]([N:18]2[CH:22]=[N:21][CH:20]=[N:19]2)(O)[C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:4][CH:3]=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1>N1C=CC=CC=1>[N:18]1([C:10]([C:11](=[O:16])[C:12]([CH3:14])([CH3:13])[CH3:15])=[CH:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:23])[CH:22]=[N:21][CH:20]=[N:19]1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 20295039HCID 20295039, compound

Product 1

HCID 53697721HCID 53697721, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A suspension of the product (16.7 g) of Stage 1 in pyridine (100 ml) was treated with p-toluene sulphonyl chloride (11 g) and shaken vigorously. The mixture was allowed to stand for 8 days with occasional shaking, during which time the solid dissolved and a dark red solution was obtained. The solution was then quenched with 2 N-hydrochloric acid (500 ml) and the resultant solid filtered off, washed with water and dried. Crystallization from petroleum ether gave the title product (15.4 g; 97%), m.p. 140°-140.5°.

Workup

  1. dissolutionthe solid dissolved
  2. customa dark red solution was obtained
  3. customThe solution was then quenched with 2 N-hydrochloric acid (500 ml)
  4. filtrationthe resultant solid filtered off
  5. washwashed with water
  6. customdried
  7. customCrystallization from petroleum ether

Sources & evidence

ORD record
ord-2c20b23de082465ab0fd84fc99589fea
Source dataset
uspto-grants-1981_01
Patent number
US04246020

Reaction notes

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