Water → HCID 28665340, compound

HRID 1727382Notes

Reaction equation

HRID 1727382 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)=[CH:6][CH:5]=1)([OH:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][CH3:27].O>CN(C=O)C>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)=[CH:6][CH:5]=1)([O:3][CH2:26][CH3:27])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 9766784-benzothiazol-2-ylbenzoic Acid

Product 1

HCID 28665340HCID 28665340, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a slurry of 2-(4-carboxyphenyl)benzothiazole (4.5 g, 17 mmol.) in DMF (38 mL), potassium carbonate (5.39 g, 39 mmol) was added and the mixture was cooled in an ice bath. Bromoethane (7.2 mL, 102 mmol) was added in portions, and the mixture was allowed to come to room temperature. After 48 hours, the mixture was poured into water and the separated solids (4.51 g) were collected. A solution of the crude product was passed through a column of silica gel. The product residue (4.19 g), left after evaporation of the solvent, was recrystallized from ethanol; 3.96 g (81% yield), m.p. 132-133.6° C. Mass spec: m/z 283 (M+). Anal. Calcd for C16H13NO2S: C, 67.83; H, 4.62; N, 4.94; S, 11.31%. Found, C, 67.86; H, 4.62; N, 4.89; S, 11.45%. FT-IR (KBr; cm−1): 3100 (sp2C—H), 2989 (sp3C—H), 1710 (C═O), 1522 (asym NO2), 1341 (sym NO2), 1279 (C—O—C), 1108, 773, 753, 696. 1H NMR (CDCl3; δ in ppm): 1.45 (t, 3H, methyl), 4.45 (q, 2H, OCH2), 7.4-7.55 (m, 2 ArH), 7.9 (d, 1 ArH), 8.05-8.20 (m, 5 ArH). 13C NMR (CDCl3; δ in ppm): 14.76, 61.72 (sp3 C), 122.12, 123.99, 126.09, 126.99, 127.78, 130.61, 132.79, 135.67, 137.67, 137.74, 154.51, 166.32 (sp2C).

Workup

  1. temperaturethe mixture was cooled in an ice bath
  2. customto come to room temperature
  3. customthe separated solids (4.51 g) were collected
  4. waitThe product residue (4.19 g), left
  5. customafter evaporation of the solvent
  6. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-1b67f155bedb4fd5bccbc17a7d55f296
Source dataset
uspto-grants-2009_02
Patent number
US07495106B1

Reaction notes

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