Sulfuric Acid → 2-[(2-Hydroxyphenyl)sulfanyl]-4-nitrobenzoic acid

HRID 255924

Reaction equation

HRID 255924 reaction equation
N[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=[O:12].S(=O)(=O)(O)[OH:22].N([O-])=O.[Na+].F[B-](F)(F)F.[Na+]>O>[OH:22][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=[O:12]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 4343483Sodium TetrafluoroborateHCID 135363082-[(2-Aminophenyl)sulfanyl]-4-nitrobenzoic acidHCID 23668193Sodium Nitrite

Product 1

HCID 135363092-[(2-Hydroxyphenyl)sulfanyl]-4-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Suspend 10.15 g (35 mmoles) of the amino acid of Step A in 75 ml of water and add 4 ml concentrated sulfuric acid (7.36 g, 75 mmoles, 140 meq.). Cool the mixture in an ice-bath and add 3.657 g (53 mmoles) of sodium nitrite in portions at 0°-5° C. Stir the suspension in the cold for 20 minutes. Add 10 g (91 mmoles) of sodium fluoroborate and stir for an additional 20 minutes. Separate the precipitated crude diazonium fluoroborate, suspend tne precipitate in 250 ml of 50% sulfuric acid and heat in an oil bath at 90°-100° C. for 45 minutes. Cool the mixture and separate the precipitate. (Yield: 7.76 g).

Workup

  1. temperatureCool the mixture in an ice-bath
  2. stirringstir for an additional 20 minutes
  3. customSeparate the
  4. customprecipitated crude diazonium fluoroborate
  5. temperatureheat in an oil bath at 90°-100° C. for 45 minutes
  6. temperatureCool the mixture
  7. customseparate the precipitate

Sources & evidence

ORD record
ord-6e9159bd06cb47f5b7e40c605f2fb209
Source dataset
uspto-grants-1987_10
Patent number
US04699917

Linked notes

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