Sodium Hydroxide → HCID 59320447, compound

HRID 655233Notes

Reaction equation

HRID 655233 reaction equation
C[O:2][C:3](=[O:15])[CH:4]([C:6]1[CH:14]=[CH:13][C:9]2[N:10]=[CH:11][S:12][C:8]=2[CH:7]=1)[CH3:5].[OH-].[Na+]>C(OCC)(=O)C>[S:12]1[C:8]2[CH:7]=[C:6]([CH:4]([CH3:5])[C:3]([OH:15])=[O:2])[CH:14]=[CH:13][C:9]=2[N:10]=[CH:11]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68703007HCID 68703007, compound

Product 1

HCID 59320447HCID 59320447, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-benzothiazol-6-yl-propionic acid methyl ester (6.6 g, 30.0 mmol) and aqueous 2 N NaOH (23.0 ml) was heated at reflux for 1 hour until the reaction mixture became a dark red solution. The mixture was then cooled to room temperature and the mixture extracted with dichloromethane (×2) and the aqueous layer was acidified with conc.hydrochloric acid to pH4-5. The resulting solid was filtered off to afford the crude product, which was stirred in ethyl acetate the filtered and dried in vacuo to provide the title compound (4.3 g, 69.2%) as an off white solid. (300 MHz, DMSO-d6): δ 12.41 (s, 1H), 9.35 (s, 1H), 8.09-8.08 (d, J=1.5 Hz, 2H), 8.05-8.02 (d, J=8.7 Hz 2H), 7.48-7.45 (dd, J=1.5 Hz, 8.7 Hz, 1H), 3.89 (q, 1H), 1.45 (d, 3H). MS m/z 208 (M++1).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour until the reaction mixture
  3. extractionthe mixture extracted with dichloromethane (×2)
  4. filtrationThe resulting solid was filtered off
  5. customto afford the crude product, which
  6. filtrationfiltered
  7. customdried in vacuo

Sources & evidence

ORD record
ord-d07935848b2340f4a815f4c55905cbff
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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