Sodium Chloride → Ethyl 2-hydroxy-5-[(4-chlorosulfonylphenyl]ethynyl]benzoate

HRID 1464179Notes

Reaction equation

HRID 1464179 reaction equation
[K].[OH:2][C:3]1[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]2[CH:21]=[CH:20][C:19]([S:22]([OH:25])(=O)=[O:23])=[CH:18][CH:17]=2)=[CH:10][C:4]=1[C:5]([O:7][CH2:8][CH3:9])=[O:6].CN(C)C=O.S(Cl)([Cl:33])=O.[Cl-].[Na+]>C1(C)C=CC=CC=1>[OH:2][C:3]1[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]2[CH:21]=[CH:20][C:19]([S:22]([Cl:33])(=[O:25])=[O:23])=[CH:18][CH:17]=2)=[CH:10][C:4]=1[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 86747767Ethyl 2-hydroxy-5-[(4-sulfophenyl]ethynyl]benzoate potassium salt

Product 1

HCID 19423376Ethyl 2-hydroxy-5-[(4-chlorosulfonylphenyl]ethynyl]benzoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Ethyl 2-hydroxy-5-[(4-sulfophenyl]ethynyl]benzoate potassium salt (19 g, 50 mmol) was suspended in toluene (100 ml). Dimethylformamide (1 ml) and thionyl chloride (12 g) were added and the suspension was refluxed for 1 h. The reaction mixture was added to a nearly saturated sodium chloride solution and the precipitated oil was extracted with toluene. The solution was dried and taken to dryness. The product was sufficiently pure for the next step. Yield 16 g, 88%.

Workup

  1. temperaturethe suspension was refluxed for 1 h
  2. extractionthe precipitated oil was extracted with toluene
  3. customThe solution was dried

Sources & evidence

ORD record
ord-a74e8a3f83084500b58a1755a1dc608e
Source dataset
uspto-grants-1994_04
Patent number
US05302718

Reaction notes

Loading…