Water → HCID 20461206, compound

HRID 543893Notes

Reaction equation

HRID 543893 reaction equation
[S:1]=[C:2]1[N:6]([CH2:7][CH2:8][C:9]#N)[C:5]2[CH:11]=[CH:12][CH:13]=[CH:14][C:4]=2[S:3]1.S(=O)(=O)(O)[OH:16].[OH2:20]>>[S:1]=[C:2]1[N:6]([CH2:7][CH2:8][C:9]([OH:16])=[O:20])[C:5]2[CH:11]=[CH:12][CH:13]=[CH:14][C:4]=2[S:3]1

Participants

4

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 2756743-(2-Thioxo-benzothiazol-3-yl)-propionitrile

Product 1

HCID 20461206HCID 20461206, compoundYield 96%

Conditions

Temperature
25 °C

Procedure

A stirred charge containing 44 g (0.2 mol) of 2-thioxo-3-benzothiazolinepropionitrile and 600 ml of 30% sulfuric acid (by volume) was heated at reflux (114°-116° C.) for 2 hours. After cooling to 25° C., 400 ml of water was added and stirring continued at 25°-30° C., for 15 minutes. The solid was collected by filtration, washed with water until neutral to litmus and air-dried at 50° C. The product, 2-thioxo-3(2H)-benzothiazolepropionic acid, m.p. 164°-165° C., was obtained in 96% yield, after recrystallization from NaOH/HCl, m.p. 167°-168° C.

Workup

  1. additionA stirred charge
  2. temperaturewas heated
  3. temperatureat reflux (114°-116° C.) for 2 hours
  4. filtrationThe solid was collected by filtration
  5. washwashed with water until neutral to litmus and
  6. customair-dried at 50° C

Sources & evidence

ORD record
ord-2830ea8522d34350b6e11b9c5181cd80
Source dataset
uspto-grants-1984_05
Patent number
US04447618

Reaction notes

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