Propanal → HCID 53939654, compound

HRID 231678Notes

Reaction equation

HRID 231678 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2[S:16][C:15]([S:17]([NH2:20])(=[O:19])=[O:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[CH:21](=O)[CH2:22][CH3:23]>C(O)C.[Pt]=O>[CH2:21]([NH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2[S:16][C:15]([S:17]([NH2:20])(=[O:18])=[O:19])=[CH:14][CH:13]=2)(=[O:10])=[O:11])=[CH:5][CH:4]=1)[CH2:22][CH3:23]

Participants

5

Reactant 2

HCID 527PropanalHCID 20033709HCID 20033709, compound

Product 1

HCID 53939654HCID 53939654, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

5-[4-aminomethylphenylsulfonyl]thiophene-2-sulfonamide (1.9 g, 5.15 mmol) and propionaldehyde (0.314 g, 5.40 mmol) were dissolved in ethanol (75 ml). Platinum oxide (300 mg) was added and the mixture was hydrogenated in a Parr apparatus at about 65 psi (96 Nm-2) for about 2 hours. The mixture was filtered through a filter aid and evaporated to dryness. The residual oil was chromatographed (50 mm×5 in, 230-400 mesh silica gel; chloroform methanol, 9 to 1 respectively) and the appropriate fractions were combined and treated with methanolic HCl. Evaporation of the solvent left a white solid which after drying for 2 hours under high vacuum at room temperature, had m.p. 151°-153° C. Anal Calc'd. for: C14H18N2O4S3.HCl: C, 40.91; H, 4.65; N, 6.82. Found: C, 40.72; H, 4.60; N, 6.89.

Workup

  1. filtrationThe mixture was filtered through a filter aid
  2. customevaporated to dryness
  3. customThe residual oil was chromatographed (50 mm×5 in, 230-400 mesh silica gel
  4. additiontreated with methanolic HCl
  5. customEvaporation of the solvent
  6. waitleft a white solid which
  7. customafter drying for 2 hours under high vacuum at room temperature

Sources & evidence

ORD record
ord-b3d96538a586441582f00dd2db1ede5f
Source dataset
uspto-grants-1989_07
Patent number
US04847289

Reaction notes

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