HCID 67951151, compound → HCID 67951152, compound

HRID 923652Notes

Reaction equation

HRID 923652 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]2[S:9][N:10]=[C:11]([O:12][CH2:13][C:14]([O:16]C)=[O:15])[C:3]=12>Cl.O>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]2[S:9][N:10]=[C:11]([O:12][CH2:13][C:14]([OH:16])=[O:15])[C:3]=12

Participants

4

Reactant 1

HCID 67951151HCID 67951151, compound

Product 1

HCID 67951152HCID 67951152, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Ester 25 (150 mg, 0.59 mmol) was suspended in conc. HCl (3 mL) and heated with stirring at 100° C. for 5 h until hydrolysis completed. The mixture was cooled to room temperature, diluted with water (350 mL), and the precipitate was collected to give the title compound (138 mg, 98% yield). C10H10N2O3S; white solid; mp 270° C. (decomposed); IR vmax (neat) 3423, 2928, 1716, 1591, 1504, 1440, 1392, 1363, 1308, 1204, 1125, 1038, 985, 862 cm−1; 1H NMR (400 MHz, DMSO-d6) δ 7.20 (1H, s), 5.03 (2H, s), 2.66 (3H, s), 2.58 (3H, s); 13C NMR (100 MHz, DMSO-d6) δ 171.0, 169.0, 160.9, 160.6, 145.3, 121.7, 115.1, 64.4, 24.1, 14.4; ESI-HRMS (negative mode) calcd for C10H6N2O3S: 237.0334. found: m/z 237.0332 [M−H]−.

Workup

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

Sources & evidence

ORD record
ord-0935cef77d62448788f5f808ce7371b4
Source dataset
uspto-grants-2016_03
Patent number
US09278982B2

Reaction notes

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