Ethanol → HCID 15670597, compound

HRID 649241Notes

Reaction equation

HRID 649241 reaction equation
O.[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:12][CH2:13][CH:14]=O.C([O:23][NH2:24])C1C=CC=CC=1.C(O)C.[C:28]1([N:34]=[C:35]=[O:36])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1(C)C=CC=CC=1>[OH:23][N:24]([CH2:14][CH2:13][O:12][C:3]1[CH:4]=[CH:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:2]=1)[C:35]([NH:34][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:36]

Participants

6

Reactant 4

HCID 702EthanolHCID 7672Phenyl isocyanateHCID 102313O-BenzylhydroxylamineHCID 86742108HCID 86742108, compound

Product 1

HCID 15670597HCID 15670597, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-naphthyloxyacetaldehyde hydrate (9.85 g), benzyloxyamine (5.94 g) and ethanol (100 ml) was stirred overnight under nitrogen to precipitate 11.21 g of the protected oxime, m.pt. 68°-69.5° C. The oxime (10.1 g) in acetic acid (100 ml) was reduced with sodium cyanoborohydride, then the isolated O-benzyl hydroxylamine, without purification, was treated with phenyl isocyanate (1 equivalent) in toluene for 4 hours at 110° C. The product had m.pt. 75°-77° C. after chromatography over silica gel (elution with methylene chloride) and recrystallization from SVM. Hydrogenation of the last-mentioned O-benzylhydroxyurea over 5% palladium on charcoal in ethanol containing a few drops of acetic acid provided 1-Hydroxy-1-[2-(2-naphthyloxy)ethyl]-3-phenylurea, m.pt. 165°-167° C. (from ethanol).

Workup

  1. customto precipitate 11.21 g of the protected oxime, m.pt. 68°-69.5° C
  2. customthe isolated O-benzyl hydroxylamine, without purification
  3. customover silica gel (elution with methylene chloride) and recrystallization from SVM

Sources & evidence

ORD record
ord-640d3ad6ea7a435a8cbd8964975bb569
Source dataset
uspto-grants-1988_04
Patent number
US04738986

Reaction notes

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