Hydrochloric Acid → 5-(2-Anilino-4-thiazolyl)-2,3-dihydroxybenzonitrile hydrochloride

HRID 1781916Notes

Reaction equation

HRID 1781916 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:6]=[C:7]([OH:14])[C:8]([OH:13])=[C:9]([CH:12]=1)[C:10]#[N:11])=O.[C:15]1([NH:21][C:22]([NH2:24])=[S:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[ClH:25]>CN(C)C=O>[ClH:25].[NH:21]([C:22]1[S:23][CH:2]=[C:3]([C:5]2[CH:6]=[C:7]([OH:14])[C:8]([OH:13])=[C:9]([CH:12]=2)[C:10]#[N:11])[N:24]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 676454PhenylthioureaHCID 214590655-(Bromoacetyl)-2,3-dihydroxybenzonitrile

Product 1

HCID 214591825-(2-Anilino-4-thiazolyl)-2,3-dihydroxybenzonitrile hydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.8 g of 5-(bromoacetyl)-2,3-dihydroxybenzonitrile dissolved in 25 ml of N,N-dimethylformamide are treated with N-phenylthiourea and stirred at 100° for 5 hours. Thereafter, the solvent is removed by evaporation. The residue is treated with 200 ml of 1N sodium carbonate solution and extracted three times with 100 ml of methylene chloride each time. The combined organic phases are washed with water, dried over sodium sulfate and evaporated. The residue is chromatographed on 30 g of silica gel with ethyl acetate. The thus-obtained crude product is treated with 40 ml of 1N hydrochloric acid, evaporated and crystallized from acetone. There is obtained 5-(2-anilino-4-thiazolyl)-2,3-dihydroxybenzo- nitrile hydrochloride of m.p. 245°-247°.

Workup

  1. customThereafter, the solvent is removed by evaporation
  2. additionThe residue is treated with 200 ml of 1N sodium carbonate solution
  3. extractionextracted three times with 100 ml of methylene chloride each time
  4. washThe combined organic phases are washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue is chromatographed on 30 g of silica gel with ethyl acetate
  8. customThe thus-obtained crude product
  9. customevaporated
  10. customcrystallized from acetone

Sources & evidence

ORD record
ord-21b99671dadd41de8b36e62c0a1d232f
Source dataset
uspto-grants-1997_05
Patent number
US05633371

Reaction notes

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