Water → (2-thioxo-1,3-benzothiazol-3(2H)-yl)acetic acid

HRID 543891Notes

Reaction equation

HRID 543891 reaction equation
[S:1]=[C:2]1[N:6]([CH2:7][C:8]#N)[C:5]2[CH:10]=[CH:11][CH:12]=[CH:13][C:4]=2[S:3]1.S(=O)(=O)(O)[OH:15].[OH2:19]>>[S:1]=[C:2]1[N:6]([CH2:7][C:8]([OH:15])=[O:19])[C:5]2[CH:10]=[CH:11][CH:12]=[CH:13][C:4]=2[S:3]1

Participants

4

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 13025466HCID 13025466, compound

Product 1

HCID 351524(2-thioxo-1,3-benzothiazol-3(2H)-yl)acetic acidYield 90%

Conditions

Temperature
25 °C

Procedure

A stirred slurry containing 10.3 g (0.05 mol) of 2-thioxo-3-benzothiazolineacetonitrile and 150 ml of 30% sulfuric acid (by volume) was heated at reflux for 2 hours. After cooling to 25° C., 800 ml of water was added and stirring was continued for 30 minutes at 25°-30° C. The solid was collected by filtration, washed with water until neutral to litmus, and air-dried at 25°-30° C. The product, 2-thioxo-3(2H)-benzothiazoleacetic acid was obtained in 90% yield , m.p. 187°-189° C. After recrystallization from 1,2-dichloroethane the crystals melted at 192°-193° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. filtrationThe solid was collected by filtration
  4. washwashed with water until neutral to litmus, and
  5. customair-dried at 25°-30° C

Sources & evidence

ORD record
ord-e981da842d1c429a907904da5efe244b
Source dataset
uspto-grants-1984_05
Patent number
US04447618

Reaction notes

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