3-Cyclopentyloxy-4-methoxybenzaldehyde → HCID 18971787, compound

HRID 2395409Notes

Reaction equation

HRID 2395409 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][C:4]=1[O:11][CH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1.Cl.[SH:18][C:19]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:20]=1[NH2:21]>CO.O>[CH:12]1([O:11][C:4]2[CH:5]=[C:6]([C:7]3[S:18][C:19]4[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:20]=4[N:21]=3)[CH:9]=[CH:10][C:3]=2[O:2][CH3:1])[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 27358933-Cyclopentyloxy-4-methoxybenzaldehydeHCID 14898531HCID 14898531, compound

Product 1

HCID 18971787HCID 18971787, compoundYield 72.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of (440 mg, 2 mmoles) 4-methoxy-3-cyclopentyloxy benzaldehyde and (400 mg, 2.1 mmoles) 2-mercapto-5-fluoroaniline hydrochloride was heated on a steam bath for 15 minutes. The resulting thick orange oil was cooled and dissolved in 5 ml of 10% FeCl3 in methanol and allowed to stir overnight. The reaction was diluted with water and extracted with CH2Cl2. The CH2Cl2 layer was dried and evaporated to give 760 mg of crude product which was purified on silica gel with CH2 Cl2 to give 500 mg of product. Recrystallization from isopropanol gave 140 mg of product. M.P.: 96°-97° C. Elemental Analysis Calc'd for C19H18O2NSF : Calc'd: C, 66.45; H, 5.28; N, 4.08. Found: C, 66.44; H. 5.13; N. 4.06.

Workup

  1. temperaturewas heated on a steam bath for 15 minutes
  2. temperatureThe resulting thick orange oil was cooled
  3. extractionextracted with CH2Cl2
  4. dry with materialThe CH2Cl2 layer was dried
  5. customevaporated
  6. customto give 760 mg of crude product which
  7. customwas purified on silica gel with CH2 Cl2

Sources & evidence

ORD record
ord-992ef7087e93429f81e0b8905b43f399
Source dataset
uspto-grants-1998_09
Patent number
US05814651

Reaction notes

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