Hydrochloric Acid → HCID 85982612, compound

HRID 229746Notes

Reaction equation

HRID 229746 reaction equation
Cl.[O:2]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[S:20][C:19]([N:21]=C(C2C=CC=CC=2)C2C=CC=CC=2)=[N:18][CH:17]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CO>[O:2]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[S:20][C:19]([NH2:21])=[N:18][CH:17]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 85982611HCID 85982611, compound

Product 1

HCID 85982612HCID 85982612, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

150 ml of an aqueous hydrochloric acid solution (1 M) are added to 35 g of 5-{2-[(phenoxy)methyl]phenyl}-N-(diphenylmethylene)-1,3-thiazol-2-amine, obtained in step 1.4, in solution in 250 ml of methanol, and the mixture is stirred for 18 hours at 20° C. The mixture is evaporated to dryness, the residue is taken up in diethyl ether and washed with an aqueous sodium hydroxide solution (0.5 M). The organic phase is dried over anhydrous sodium sulphate and concentrated. The residue is chromatographed on a silica gel column, eluting with a dichloromethane/methanol 98/2 (v/v) mixture, to give 15 g of a beige solid.

Workup

  1. customThe mixture is evaporated to dryness
  2. washwashed with an aqueous sodium hydroxide solution (0.5 M)
  3. dry with materialThe organic phase is dried over anhydrous sodium sulphate
  4. concentrationconcentrated
  5. customThe residue is chromatographed on a silica gel column
  6. washeluting with a dichloromethane/methanol 98/2 (v/v) mixture

Sources & evidence

ORD record
ord-da8ad5289faa40109336884e5fcb5927
Source dataset
uspto-grants-2009_07
Patent number
US07563903B2

Reaction notes

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