Potassium Carbonate → 2-[(5-chloro-1,3-benzothiazol-2-yl)sulfanyl]-N'-hydroxyethanimidamide

HRID 325978Notes

Reaction equation

HRID 325978 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10][CH2:11][C:12]#[N:13])=[N:7][C:6]=2[CH:14]=1.[ClH:15].[OH:16][NH2:17].C(=O)([O-])[O-].[K+].[K+]>C(O)C.O>[Cl:15][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10][CH2:11][C:12](=[NH:13])[NH:17][OH:16])=[N:7][C:6]=2[CH:14]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 13312471[(5-Chloro-1,3-benzothiazol-2-yl)sulfanyl]acetonitrile

Product 1

HCID 1785114642-[(5-chloro-1,3-benzothiazol-2-yl)sulfanyl]-N'-hydroxyethanimidamideYield 34%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

14.4 g (0.6 m) (5-chloro-2-benzothiazolylthio)acetonitrile, prepared according to Example 1, 4.17 g (0.06 m) hydroxyamine hydrochloride and 4.14 g (0.03 m) potassium carbonate are dissolved in a mixture of 180 ml ethanol and 2 ml water. The mixture is heated overnight and then cooled. The solid which is collected is washed with water. The crude material is recrystallized from ethanol. The recrystallized product weighs 5.6 g (34% yield) and melts at 155°-7° C.

Workup

  1. temperatureThe mixture is heated overnight
  2. temperaturecooled
  3. customThe solid which is collected
  4. washis washed with water
  5. customThe crude material is recrystallized from ethanol

Sources & evidence

ORD record
ord-926b4f0ee0774c539a63db62e586c3ed
Source dataset
uspto-grants-1984_04
Patent number
US04443606

Reaction notes

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