Water → HCID 57967172, compound

HRID 420565Notes

Reaction equation

HRID 420565 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]2[N:6]=[C:7]([N:9]3[CH2:14][CH2:13][N:12]([CH2:15][C:16]4[CH:17]=[C:18]([CH2:22][C:23]#N)[CH:19]=[CH:20][CH:21]=4)[CH2:11][CH2:10]3)[S:8][C:4]=2[CH:3]=1.S(=O)(=O)(O)O.[OH2:32].[OH-:33].[Na+]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:26]=[CH:25][C:5]2[N:6]=[C:7]([N:9]3[CH2:14][CH2:13][N:12]([CH2:15][C:16]4[CH:17]=[C:18]([CH2:22][C:23]([OH:33])=[O:32])[CH:19]=[CH:20][CH:21]=4)[CH2:11][CH2:10]3)[S:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 57966226HCID 57966226, compound

Product 1

HCID 57967172HCID 57967172, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of {3-[[4-(6-chlorobenzothiazole-2-yl)piperazine-1-yl]methyl]phenyl}acetonitrile (0.35 g; 0.914 mmol), concentrated sulfuric acid (2 ml) and water (2 ml) was stirred at 80° C. for 2 hours. After air cooling, 5N-aqueous sodium hydroxide was added thereto to be alkaline. Ethyl acetate was added thereto and back-extracted. The water layer became neutral with 2N-aqueous hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulphate, and evaporated under reduced pressure to give 3-[[4-(6-chlorobenzothiazole-2-yl)piperazine-1-yl]methyl]phenyl acetic acid as colorless amorphous solid (0.08 g; 22%).

Workup

  1. temperatureAfter air cooling
  2. extractionback-extracted
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-cc046890b7784666aecbc385578044e0
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

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