4-Aminobenzoic Acid → 4-Isothiocyanatobenzoic acid

HRID 2118767Notes

Reaction equation

HRID 2118767 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[C:11](Cl)(Cl)=[S:12]>Cl>[N:1]([C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)=[C:11]=[S:12]

Participants

4

Reactant 2

HCID 9784-Aminobenzoic AcidHCID 10040Thiophosgene

Product 1

HCID 2429464-Isothiocyanatobenzoic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A sample of p-aminobenzoic acid is dissolved in 3N HCl (20% by weight). To this is added about one equivalent of thiophosgene in a single portion. The reaction mixture is stirred until a white precipitate appears, the crude product is filtered, washed with water, and crystallized from acetone-water to give crude p-isothiocyanatobenzoic acid.

Workup

  1. filtrationthe crude product is filtered
  2. washwashed with water
  3. customcrystallized from acetone-water

Sources & evidence

ORD record
ord-02356b00b69a405d95134e8cab1c4d4a
Source dataset
uspto-grants-1987_07
Patent number
US04680338

Reaction notes

Loading…