Hydrochloric Acid → 2-Benzothiazol-2-yl-3-furan-2-yl-3-hydroxyacrylonitrile

HRID 407334Notes

Reaction equation

HRID 407334 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:25]#[N:26])=[C:11]([O:17]C(C1OC=CC=1)=O)[C:12]1[O:13][CH:14]=[CH:15][CH:16]=1.[OH-].[K+].O.Cl>C(O)C>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10](=[C:11]([C:12]1[O:13][CH:14]=[CH:15][CH:16]=1)[OH:17])[C:25]#[N:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 66768488HCID 66768488, compound

Product 1

HCID 7034362-Benzothiazol-2-yl-3-furan-2-yl-3-hydroxyacrylonitrileYield 97.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of furan-2-carboxylic acid 2-benzothiazol-2-yl-2-cyano-1-furan-2-yl-vinyl ester (660 mg, 1.82 mmol) and KOH (108 mg, 1.93 mmol) in ethanol (20 mL) was stirred first at room temperature overnight and then at 50° C. for 2 hours. The resulting suspension was poured into water (200 mL), and the solution was adjusted to pH 7 using 5% HCl solution. The solids were isolated by filtration, washed with water, and air-dried to yield 474 mg (97%) of crude 2-benzothiazol-2-yl-3-furan-2-yl-3-hydroxy acrylonitrile which was used in the next step without further purification. MS (m/z, ES+): 268.98 (M+1, 100%).

Workup

  1. waitat 50° C. for 2 hours
  2. customThe solids were isolated by filtration
  3. washwashed with water
  4. customair-dried

Sources & evidence

ORD record
ord-6cf43326f50a4d33a1b146c8d16eefe3
Source dataset
uspto-grants-2014_06
Patent number
US08754233B2

Reaction notes

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