Hydroxylamine → N'-Hydroxy-N-(1-methylethyl)-N-phenylurea

HRID 1582564Notes

Reaction equation

HRID 1582564 reaction equation
[NH2:1][OH:2].[CH3:3][CH:4]([N:6]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:7](Cl)=[O:8])[CH3:5]>C1COCC1>[OH:2][NH:1][C:7](=[O:8])[N:6]([CH:4]([CH3:5])[CH3:3])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 11446927(1-Methylethyl)phenylcarbamic chloride

Product 1

HCID 22717691N'-Hydroxy-N-(1-methylethyl)-N-phenylureaYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution, of 50% aqueous hydroxylamine (16.8 g, 0.25 mol) was added dropwise to a solution of (1-methylethyl)phenylcarbamic chloride (20.0 g, 0.1 mol) in 200 mL of THF in an ice bath so that the reaction temperature was kept below 30° C. Precipitate began to form halfway through the addition. The resulting slurry was stirred overnight. The mixture was filtered, and the solids collected were first washed with water and then with hexane/ether. After air-drying, 14.56 g of the title compound was obtained. Its structure was confirmed by an analysis of the NMR spectra. The filtrate was stripped down to afford a residue which was washed sequentially with 1N HCl, water and hexane/ether to yield a second crop of the title compound (5.38 g) melting at 165-166° C. The combined yield was 100%.

Workup

  1. customwas kept below 30° C
  2. customto form halfway
  3. additionthrough the addition
  4. filtrationThe mixture was filtered
  5. customthe solids collected
  6. washwere first washed with water
  7. customAfter air-drying

Sources & evidence

ORD record
ord-349a02fa5caf422aba950ebbacbbbb0c
Source dataset
uspto-grants-2004_05
Patent number
US06737383B1

Reaction notes

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