4-Aminobenzoic Acid → 2-(4-Aminophenyl)benzothiazole

HRID 1636551Notes

Reaction equation

HRID 1636551 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[NH2:9][C:10]1[CH:18]=[CH:17][C:13]([C:14](O)=O)=[CH:12][CH:11]=1>C(=O)(O)[O-].[Na+]>[NH2:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]2[S:8][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[N:1]=2)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 9784-Aminobenzoic AcidHCID 87132-Aminothiophenol

Product 1

HCID 2344752-(4-Aminophenyl)benzothiazoleYield 57%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
230 °C

Procedure

A stirrable paste prepared by mixing 2-aminothiophenol (9.39 g, 0.075 mol) and 4-aminobenzoic acid (10.29 g, 0.075 mol) with PPA (120 g) was heated to 230° C. for 4 hours, cooled and poured into a large volume of 10% sodium bicarbonate solution (about 1000 ml). The solid was collected by filtration, washed with water and dried. Recrystallisation from methanol gave pale yellow needed crystals (9.65 g, 57%), m.p. 155-157° C.

Workup

  1. customA stirrable paste prepared
  2. temperaturecooled
  3. filtrationThe solid was collected by filtration
  4. washwashed with water
  5. customdried
  6. customRecrystallisation from methanol

Sources & evidence

ORD record
ord-529636306fcb4ec1bd98a6b26579e551
Source dataset
uspto-grants-2000_03
Patent number
US06034246

Reaction notes

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