Hydrochloric Acid → 2-Amino-5-chlorobenzenethiol

HRID 1370499Notes

Reaction equation

HRID 1370499 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=C(N)[S:8][C:4]=2[CH:3]=1.[OH-].[K+].Cl>O>[NH2:6][C:5]1[CH:10]=[CH:11][C:2]([Cl:1])=[CH:3][C:4]=1[SH:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 72266-Chloro-2-benzothiazolamineHCID 14797Potassium Hydroxide

Product 1

HCID 27375182-Amino-5-chlorobenzenethiolYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 6-chloro-benzothiazol-2-ylamine (Example 200, 17.8 g, 96.7 mmol) and KOH (EM, 87 g, 1.55 mol) in 150 mL of water was refluxed for 2 d. The mixture was cooled to room temperature and was diluted with ice. The solution was brought to pH 5 with concentrated HCl. The mixture was extracted 3× with EtOAc (300 mL). The organic layers were combined and washed twice with a brine solution (300 mL), dried over Na2SO4. Removal of the solvent under reduced pressure gave 10.5 g product.

Workup

  1. additionwas diluted with ice
  2. extractionThe mixture was extracted 3× with EtOAc (300 mL)
  3. washwashed twice with a brine solution (300 mL)
  4. dry with materialdried over Na2SO4
  5. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-28928854000545cca9e7a6465e1854be
Source dataset
uspto-grants-2003_06
Patent number
US06583157B2

Reaction notes

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