Dimethyl Sulfoxide → 4-benzothiazol-2-ylbenzoic Acid

HRID 1727381Notes

Reaction equation

HRID 1727381 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[C:9]([C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1)([OH:11])=[O:10].CS(C)=O>O>[C:9]([C:12]1[CH:19]=[CH:18][C:15]([C:16]2[S:8][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[N:1]=2)=[CH:14][CH:13]=1)([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 87132-AminothiophenolHCID 120884-Formylbenzoic acid

Product 1

HCID 9766784-benzothiazol-2-ylbenzoic AcidYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
145 °C

Procedure

A mixture of 2-aminothiophenol (9.00 ml, 0.08 mol), 4-carboxybenzaldehyde (10.1 g, 0.07 mol) and DMSO (40 mL) was heated to 145° C., and held at this temperature for 3.5 hours. The reaction mixture was diluted with water, and separated solids were collected, dried and recrystallized from acetic acid; 14.15 g, (82% yield), white solid, m.p. 294.1-295.5° C. Mass Spectrum: m/z, 255 (M+), 238 (M—OH), 210 (M—COOH), 108. FT-IR (KBr; cm−1): 3051 (br; OH), 1684 (CO), 1609, 1424, 1407, 1291, 970, 756. Anal. Calcd for C14H9NO2S: C, 65.87; H, 3.55; N, 5.49; S, 12.56%. Found: C, 65.71; H, 3.96; N, 5.30; S, 12.66%. NMR: not available due to poor solubility.

Workup

  1. customseparated solids
  2. customwere collected
  3. customdried
  4. customrecrystallized from acetic acid

Sources & evidence

ORD record
ord-c3aec758c38b4cf998bd91a315757150
Source dataset
uspto-grants-2009_02
Patent number
US07495106B1

Reaction notes

Loading…