Sodium Hydroxide → HCID 19967416, compound

HRID 976646Notes

Reaction equation

HRID 976646 reaction equation
Cl.[CH2:2]([O:9][NH2:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[Na+].[CH3:13][N:14]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:15](Cl)=[O:16]>O.C(OCC)C.C(=O)(O)[O-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>[CH2:2]([O:9][NH:10][C:15]([N:14]([CH3:13])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:16])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

8

Reactant 3

HCID 14798Sodium HydroxideHCID 77969Carbamic chloride, N-methyl-N-phenyl-HCID 102312Benzyloxyamine hydrochloride

Product 1

HCID 19967416HCID 19967416, compoundYield 64.3%

Reagents, catalysts & solvents 4

HCID 962WaterSolvent3×HCID 3283Diethyl EtherSolvent2×HCID 10340Sodium CarbonateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

O-Benzylhydroxylamine hydrochloride (3.0 g, 18.8 mmole) was dissolved in water (3.5 mL) then combined with diethyl ether (85 mL) followed by the addition of sodium hydroxide (0.75 g, 18.8 mmole) in water. After several minutes a solution of N-methyl-N-phenylcarbamoyl chloride (3.19 g, 18.8 mmole) in diethyl ether (25 mL) was added. A white precipitate formed. The solid was isolated by filtration then dissolved in water. The solution was diluted with saturated aqueous sodium bicarbonate and sufficient solid sodium carbonate was added to bring the pH to 9. The solution was extracted with diethyl ether (5×50 mL). The ether extracts were combined, dried and then concentrated to provide the crude product as a beige solid. The crude product was purified by silica gel chromatography (9:1 hexanes/ethyl acetate) to provide 3.1 g of 1-benzyloxy-3-methyl-3-phenylurea.

Workup

  1. customA white precipitate formed
  2. customThe solid was isolated by filtration
  3. additionwas added
  4. extractionThe solution was extracted with diethyl ether (5×50 mL)
  5. customdried
  6. concentrationconcentrated
  7. customto provide the crude product as a beige solid
  8. customThe crude product was purified by silica gel chromatography (9:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-c1360d9585b3435188c5773fff71974c
Source dataset
uspto-grants-1997_03
Patent number
US05612377

Reaction notes

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