Phenol → HCID 21487310, compound

HRID 1414392Notes

Reaction equation

HRID 1414392 reaction equation
Cl[C:2]1[CH:9]=[C:8](Cl)[C:7]([S:11](=[O:14])(=[O:13])[NH2:12])=[CH:6][C:3]=1[C:4]#[N:5].[C:15]1([OH:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[OH-:22].[Na+]>CN(C)C=O>[O:21]([C:2]1[CH:9]=[C:8]([O:22][C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:3]=2)[C:7]([S:11](=[O:14])(=[O:13])[NH2:12])=[CH:6][C:3]=1[C:4]#[N:5])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 14798Sodium HydroxideHCID 21430435HCID 21430435, compound

Product 1

HCID 21487310HCID 21487310, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 251 g of 2,4-dichloro-5-sulfamoyl-benzonitrile (1.0 mol), 400 ml of dimethylformamide, 200 g of phenol and 80 g of sodium hydroxide was stirred for 3 hours at 130° C. The mixture was then allowed to cool to about 90° C and when its viscosity was low and it was turbid from precipitated NaCl, it was introduced into 10 l of water. After having been allowed to stand for 1 hour at room temperature, the light grey crystallized precipitate was suction-filtered, washed several times with water, and the product still moist after filtration was then recrystallized from isopropanol. The product was first dried in the air and then on a steam bath until its weight remained constant. The colorless crystals thus obtained still contained one mol-equivalent of isopropanol.

Workup

  1. temperatureto cool to about 90° C
  2. customfrom precipitated NaCl, it
  3. additionwas introduced into 10 l of water
  4. waitto stand for 1 hour at room temperature
  5. filtrationthe light grey crystallized precipitate was suction-filtered
  6. washwashed several times with water
  7. filtrationthe product still moist after filtration
  8. customwas then recrystallized from isopropanol
  9. customThe product was first dried in the air
  10. customon a steam bath until its weight remained constant
  11. customThe colorless crystals thus obtained still contained one mol-equivalent of isopropanol

Sources & evidence

ORD record
ord-5fca3baf5ef343518da87edb39afd7dc
Source dataset
uspto-grants-1977_01
Patent number
US04001284

Reaction notes

Loading…