HCID 11148787, compound → (3-Oxo-1,2-benzothiazol-2(3H)-yl)acetic acid

HRID 923640Notes

Reaction equation

HRID 923640 reaction equation
[O:1]=[C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[S:4][N:3]1[CH2:11][C:12]([O:14]C)=[O:13]>Cl.O>[O:1]=[C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[S:4][N:3]1[CH2:11][C:12]([OH:14])=[O:13]

Participants

4

Reactant 1

HCID 11148787HCID 11148787, compound

Product 1

HCID 14451760(3-Oxo-1,2-benzothiazol-2(3H)-yl)acetic acidYield 98.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Ester 6 (500 mg, 2.24 mmol) was suspended in conc. HCl (8 mL) and heated with stirring at 100° C. for 6 h until hydrolysis completed.4 The mixture was cooled to room temperature, diluted with water (500 mL), and the precipitate was collected to give the title compound (460 mg, 98% yield). C9H7NO3S; white solid; mp 241-243° C.; 1H NMR (400 MHz, CDCl3) δ 7.97 (1H, dt, J=8, 0.8 Hz), 7.79 (1H, dt, J=8, 0.8 Hz), 7.70 (1H, td, J=8, 1.2 Hz), 7.46 (1H, td, J=8, 1.2 Hz), 4.64 (2H, s); 13C NMR (100 MHz, CDCl3) δ 169.4, 166.4, 141.8, 132.3, 125.8, 125.5, 123.4, 121.0, 44.4; ESI-HRMS (negative mode) calcd for C9H7NO3S: 208.0068. found: m/z 208.0064 [M−H]−.

Workup

  1. temperatureheated
  2. temperaturewas cooled to room temperature
  3. customthe precipitate was collected

Sources & evidence

ORD record
ord-73389b0a23c74a3b9faa1c356c95a0ba
Source dataset
uspto-grants-2016_03
Patent number
US09278982B2

Reaction notes

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