Hydrochloric Acid → {2-[(3-Phenoxybenzyl)thio]-4,5,6,7-tetrahydro-1,3-benzothiazol-7-yl}acetic acid

HRID 1163323Notes

Reaction equation

HRID 1163323 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:33]=[CH:34][CH:35]=1)[CH2:11][S:12][C:13]1[S:14][C:15]2[CH:21]([CH:22](C(OCC)=O)[C:23]([O:25]CC)=[O:24])[CH2:20][CH2:19][CH2:18][C:16]=2[N:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C(O)(=O)C>[O:1]([C:8]1[CH:9]=[C:10]([CH:33]=[CH:34][CH:35]=1)[CH2:11][S:12][C:13]1[S:14][C:15]2[CH:21]([CH2:22][C:23]([OH:25])=[O:24])[CH2:20][CH2:19][CH2:18][C:16]=2[N:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58755254Diethyl {2-[(3-phenoxybenzyl)thio]-4,5,6,7-tetrahydro-1,3-benzothiazol-7-yl}malonate

Product 1

HCID 23111684{2-[(3-Phenoxybenzyl)thio]-4,5,6,7-tetrahydro-1,3-benzothiazol-7-yl}acetic acidYield 92%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of diethyl {2-[(3-phenoxybenzyl)thio]-4,5,6,7-tetrahydro-1,3-benzothiazol-7-yl}malonate (1.21 g, 2.36 mmol), 37% hydrochloric acid (10 mL) and acetic acid (10 mL) was heated with stirring at 120° C. for 12 hr. The reaction mixture was concentrated, and the residue was diluted with ethyl acetate, washed successively with 10% aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the title compound (890 mg, 92%) as a pale-yellow oil.

Workup

  1. temperaturewas heated
  2. concentrationThe reaction mixture was concentrated
  3. additionthe residue was diluted with ethyl acetate
  4. washwashed successively with 10% aqueous sodium hydrogen carbonate solution and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2deb74e59eef4e67bb03f675ea817125
Source dataset
uspto-grants-2010_10
Patent number
US07820837B2

Reaction notes

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