Hydroxylamine → HCID 20491440, compound

HRID 1278163Notes

Reaction equation

HRID 1278163 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:19]=[C:20]=[O:21])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1.[NH2:22][OH:23]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:19][C:20](=[O:21])[NH:22][OH:23])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 20491439HCID 20491439, compound

Product 1

HCID 20491440HCID 20491440, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Fourteen grams of 3-chloro-4-(2-naphthyloxy)phenyl isocyanate were dissolved in 60 ml of methylene chloride, and the resulting solution was added dropwise to 10 ml of an aqueous solution containing 4 g of hydroxylamine at a temperature below 20° C. Precipitated crystals were collected on a filter, washed with water and dried to obtain 13.5 g of N'-[3-chloro-4-(2-naphthyloxy)phenyl]-N-hydroxyurea. Thereafter, 13.5 g of the product was dissolved in 150 ml of a benzene-methanol (1:1) mixture, and 13 ml of dimethyl sulfate and 30 ml of 10 N sodium hydroxide were alternately added dropwise thereto at a temperature below 30° C. After stirring at room temperature, the reaction mixture was diluted with water, followed by extraction with benzene. The benzene layer was washed with water, and the solvent was removed under reduced pressure. The oily substance obtained was purified by column chromatography (silica gel, 100-120 mesh; eluting solvent, tetrahydrofuran-benzene (1:1) mixture) to obtain 7.3 g of N'-[3-chloro-4-(2-naphthyloxy)phenyl]-N-methoxy-N-methylurea. nD25.0 :1.5860.

Workup

  1. customPrecipitated crystals
  2. customwere collected on a filter
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-879336fa947f44ffbb21a3c1245b31db
Source dataset
uspto-grants-1981_07
Patent number
US04280835

Reaction notes

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