Hydrochloric Acid → HCID 22283427, compound

HRID 2250799Notes

Reaction equation

HRID 2250799 reaction equation
COC(=O)[NH:4][C:5]1[S:6][C:7]2[C:13]([C:14]3[CH:19]=[CH:18][N:17]=[C:16]([CH3:20])[CH:15]=3)=[CH:12][CH:11]=[C:10]([O:21][CH3:22])[C:8]=2[N:9]=1.[OH-].[K+].Cl>C(O)CO.O>[CH3:22][O:21][C:10]1[C:8]2[N:9]=[C:5]([NH2:4])[S:6][C:7]=2[C:13]([C:14]2[CH:19]=[CH:18][N:17]=[C:16]([CH3:20])[CH:15]=2)=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 86584954HCID 86584954, compound

Product 1

HCID 22283427HCID 22283427, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

[4-Methoxy-7-(2-methyl-pyridin-4-yl)-benzothiazol-2-yl]-carbamic acid methyl ester (100 mg, 0.24 mmol) were dissolved in ethyleneglycol (3.0 ml) and treated with potassium hydroxide (528 mg, 1.1 mmol) and heated to 100° C. for 6.5 h. The reaction mixture was cooled to room temperature, diluted with water, neutralized with 1N HCl and extracted four times with ethyl acetate. The organic layers were combined and washed with water and saturated aqueous NaCl. The organic phases were then dried and the solvent removed in vacuo. The product was obtained as a light brown solid (83%). MS: m/e=272 (M+H+).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted four times with ethyl acetate
  3. washwashed with water and saturated aqueous NaCl
  4. customThe organic phases were then dried
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-8fe3b23ceb2d4e81acbd5f231f0eb508
Source dataset
uspto-grants-2008_01
Patent number
US07317007B2

Reaction notes

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