4-Toluenesulfonyl chloride → HCID 21406337, compound

HRID 972208Notes

Reaction equation

HRID 972208 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[CH2:11][CH2:12][C:13](=[O:16])[NH:14][N:15]=2)[CH:5]=[C:6]([Cl:9])[C:7]=1[OH:8].[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.C(N(CC)CC)C>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[CH2:11][CH2:12][C:13](=[O:16])[NH:14][N:15]=2)[CH:5]=[C:6]([Cl:9])[C:7]=1[O:8][S:23]([C:20]1[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=1)(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 136409735HCID 136409735, compound

Product 1

HCID 21406337HCID 21406337, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 10 g. of 6-(3,5-dichloro-4-hydroxyphenyl)-4,5-dihydro-3(2H)pyridazinone, 7.6 g. of p-toluenesulfonic chloride, 4 g. of triethylamine and 50 ml. of dimethylformamide was stirred at 50° C. for 8 hours. Then, the reaction mixture was treated in the same manner as in Example 11 and recrystallized from dioxane-petroleum ether to give 3.8 g. of the desired product as prisms of m.p. 208° - 209° C.

Workup

  1. additionA mixture of 10 g
  2. additionThen, the reaction mixture was treated in the same manner as in Example 11
  3. customrecrystallized from dioxane-petroleum ether
  4. customto give 3.8 g

Sources & evidence

ORD record
ord-764af15aa2a64b6e8c9098c4c9d61d69
Source dataset
uspto-grants-1977_10
Patent number
US04052395

Reaction notes

Loading…