Water → Benzo[d]thiazole-5-carboxamide

HRID 1507541Notes

Reaction equation

HRID 1507541 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]#[N:11])=[CH:9][C:4]=2[N:3]=[CH:2]1.O.C(=O)(O)[O-:14].[Na+]>S(=O)(=O)(O)O>[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([NH2:11])=[O:14])=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 107021045-Benzothiazolecarbonitrile

Product 1

HCID 68934914Benzo[d]thiazole-5-carboxamide

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 1,3-benzothiazole-5-carbonitrile (100 mg, 0.62 mmol, 1.00 equiv) in sulfuric acid (3.0 mL) was heated for 2 h at 45° C. After cooling down, the reaction mixture was poured into 15 mL of water. The pH value of the solution was adjusted to 7 with saturated aqueous sodium bicarbonate. The resulting solution was extracted with of ethyl acetate (5×10.0 mL). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and then concentrated under vacuum. This resulted in 60.0 mg of the title compound as a crude product, which was used directly for next step without further purification. MS m/z [M+H]+ (ESI): 179.

Workup

  1. temperatureAfter cooling down
  2. extractionThe resulting solution was extracted with of ethyl acetate (5×10.0 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a739b01ce8dc41a99840d6e9c4c82abb
Source dataset
uspto-grants-2015_12
Patent number
US09221809B2

Reaction notes

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