Benzaldehyde → HCID 21506093, compound

HRID 1287803Notes

Reaction equation

HRID 1287803 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:18](=[O:24])(=[O:23])[NH:19][C:20](=[O:22])[CH3:21])[C:10]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:5]([OH:7])=[O:6].[CH:25](=O)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[H][H]>[Pt]=O.C(O)(=O)C>[C:20]([NH:19][S:18]([C:9]1[C:10]([O:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[C:2]([NH:1][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:3]=[C:4]([CH:8]=1)[C:5]([OH:7])=[O:6])(=[O:24])=[O:23])(=[O:22])[CH3:21]

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 21506080HCID 21506080, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 21506093HCID 21506093, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 3-amino-5-acetylsulphamyl-4-phenoxy-benzoic acid (1 g), benzaldehyde (0.3 g), and acetic acid (40 ml) was heated on a steam bath for 2 hours. After cooling to room temperature, platinum oxide catalyst (0.035 mg) was added, and the reaction mixture was hydrogenated at room temperature and at 1.1 atmospheres hydrogen pressure. After the hydrogen uptake had become negligible, the catalyst was removed by filtration, and the filtrate evaporated in vacuo. After several recrystallizations of the residue from aqueous ethanol, and after drying in vacuo at 76° C, the compound was obtained with a melting point of 241°-243° C. The compound crystallized as a hemi-hydrate.

Workup

  1. temperaturewas heated on a steam bath for 2 hours
  2. customthe catalyst was removed by filtration
  3. customthe filtrate evaporated in vacuo
  4. customAfter several recrystallizations of the residue from aqueous ethanol
  5. customafter drying in vacuo at 76° C
  6. customthe compound was obtained with a melting point of 241°-243° C
  7. customThe compound crystallized as a hemi-hydrate

Sources & evidence

ORD record
ord-cac7f82bc8c9496295928c88486bb074
Source dataset
uspto-grants-1976_10
Patent number
US03985777

Reaction notes

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