P-Toluic Acid → 2-(4-Methylphenyl)-1,3-benzothiazole

HRID 224314Notes

Reaction equation

HRID 224314 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[CH3:9][C:10]1[CH:11]=[CH:12][C:13]([C:16](O)=O)=[CH:14][CH:15]=1.[OH-].[Na+]>O>[S:8]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=[C:9]1[C:10]1[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 7470P-Toluic AcidHCID 87132-AminothiophenolHCID 14798Sodium Hydroxide

Product 1

HCID 9193852-(4-Methylphenyl)-1,3-benzothiazoleYield 76.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

125 g (1 mol) of o-aminothiophenol, 136 g (1 mol) of p-toluic acid and 600 g of polyphosphoric acid were admixed and stirred into nitrogen gas at 170°-200° C. for 4 hours. After the reaction mixture was cooled to 100° C., it was poured in 5 l of water. The mixture was adjusted to pH 5 with NaOH and the resulting crystals were filtered off, whereupon 220 g of 4-(benzothiazol-2-yl) toluene was obtained as crude crystals. Recrystallization from n-hexane gave 172 g of pure product as colorless prisms melting at 84°-85° C.

Workup

  1. filtrationthe resulting crystals were filtered off, whereupon 220 g of 4-(benzothiazol-2-yl) toluene
  2. customwas obtained as crude crystals
  3. customRecrystallization from n-hexane

Sources & evidence

ORD record
ord-3664ea20ddb445efa7932149b3b1eaec
Source dataset
uspto-grants-1980_11
Patent number
US04232010

Reaction notes

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