Benzene → Methyl 3-{2-[4-(chlorosulfonyl)phenyl]hydrazinylidene}-6-oxocyclohexa-1,4-diene-1-carboxylate

HRID 442300Notes

Reaction equation

HRID 442300 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[N:9][C:10]2[CH:15]=[CH:14][C:13]([S:16]([O-])(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[CH:4][C:3]=1[C:20]([O:22][CH3:23])=[O:21].[K+].C1C=CC=CC=1.CN(C)C=O.S(Cl)([Cl:38])=O>O>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[N:9][C:10]2[CH:15]=[CH:14][C:13]([S:16]([Cl:38])(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[CH:4][C:3]=1[C:20]([O:22][CH3:23])=[O:21]

Participants

6

Reactant 4

HCID 241BenzeneHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 135850739Potassium 4-(4-hydroxy-3-carbomethoxy-phenylazo)-benzenesulphonate

Product 1

HCID 135850738Methyl 3-{2-[4-(chlorosulfonyl)phenyl]hydrazinylidene}-6-oxocyclohexa-1,4-diene-1-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

17.6 g of potassium 4-(4-hydroxy-3-carbomethoxy-phenylazo)-benzenesulphonate, 30 ml of benzene, 2 ml of dimethylformamid and 6 ml of thionyl chloride are heated to the boiling point under reflux for 30 min. The mixture is cooled, and cold water and 100 ml of petroleum ether are added with rapid stirring. The product is filtered off and washed with water and dried, whereupon 15.4 g of the title compound are obtained. The melting point is 137° - 138° C. after recrystallization.

Workup

  1. temperatureunder reflux for 30 min
  2. temperatureThe mixture is cooled
  3. filtrationThe product is filtered off
  4. washwashed with water
  5. dry with materialdried, whereupon 15.4 g of the title compound
  6. customare obtained
  7. customThe melting point is 137° - 138° C. after recrystallization

Sources & evidence

ORD record
ord-b0e8d6b074ad419f98083010f4a5ee65
Source dataset
uspto-grants-1977_08
Patent number
US04045429

Reaction notes

Loading…