Hydrochloric Acid → 2-Chloro-4-(4-fluorosulfonylphenylazo)phenol

HRID 263150Notes

Reaction equation

HRID 263150 reaction equation
[S:1]([F:11])(=[O:10])([C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1)=[O:2].Cl.[N:13]([O-])=O.[Na+].[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[OH:24]>O.N1C=CC=CC=1>[Cl:17][C:18]1[CH:23]=[C:22]([N:13]=[N:9][C:6]2[CH:5]=[CH:4][C:3]([S:1]([F:11])(=[O:10])=[O:2])=[CH:8][CH:7]=2)[CH:21]=[CH:20][C:19]=1[OH:24]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 72452-ChlorophenolHCID 668234-Aminobenzenesulfonyl fluorideHCID 23668193Sodium Nitrite

Product 1

HCID 1356774452-Chloro-4-(4-fluorosulfonylphenylazo)phenol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

Sulfanilyl fluoride (17.5 g, 0.1 mole) was dissolved in 75 ml warn saturated methanolic HCl, and the resulting solution was cooled in a methanol-ice bath. Sodium nitrite (7.0 g, 0.1 mole), dissolved in 25 ml water was then added dropwise, and the solution stirred 5 minutes more. The diazonium salt solution was then added dropwise to a cold (cooled in an ice bath) solution of o-chlorophenol (12.8 g, 0.099 mole) dissolved in 150 ml pyridine. The reaction mixture was stirred an additional 15 minutes and then poured over ice and hydrochloric acid. The resulting precipitate was filtered off, washed with water, and air dried. The yield was 20.0 g (64%), m.p. 133°-134° C.

Workup

  1. temperaturethe resulting solution was cooled in a methanol-ice bath
  2. additionwas then added dropwise
  3. stirringThe reaction mixture was stirred an additional 15 minutes
  4. filtrationThe resulting precipitate was filtered off
  5. washwashed with water, and air
  6. customdried

Sources & evidence

ORD record
ord-d0bf26c8d89c4d8ea4482efe0fc4d255
Source dataset
uspto-grants-1979_05
Patent number
US04156609

Reaction notes

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