Formamide → N-((4-(Benzyloxy)phenyl)(tosyl)methyl)formamide

HRID 33913

Reaction equation

HRID 33913 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.[CH2:11]([O:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH:27]([NH2:29])=[O:28]>CO>[CH2:11]([O:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]([S:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)(=[O:10])=[O:9])[NH:29][CH:27]=[O:28])=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 713FormamideHCID 10818p-Toluenesulfinic acidHCID 78109Benzaldehyde, 4-(phenylmethoxy)-

Product 1

HCID 59797510N-((4-(Benzyloxy)phenyl)(tosyl)methyl)formamideYield 49%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-methylbenzenesulfinic acid (3.1 g, 19.9 mmol), 4-(benzyloxy)benzaldehyde (4.2 g, 19.9 mmol), and formamide (4.5 mL ) was heated at 60° C. for 20 h. The mixture was diluted with methanol and stirring was continued for 1 h at rt. The resultant solid was filtered and dried to give 3.81 g (49%) of a white solid. The product was used in the next step without future purification.

Workup

  1. filtrationThe resultant solid was filtered
  2. customdried

Sources & evidence

ORD record
ord-89e71a12bdda428480b51ec0550a9332
Source dataset
uspto-grants-2008_09
Patent number
US07429665B2

Linked notes

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