Sodium Sulfate → HCID 86690358, compound

HRID 575908Notes

Reaction equation

HRID 575908 reaction equation
C(O[CH:4](OCC)[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][N:12]([CH3:20])[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:7][CH:6]=1)C.[O-]S([O-])(=O)=O.[Na+].[Na+].Cl.[NH2:32][OH:33]>CC1OCCC1.CC(OC)(C)C>[OH:33][N:32]=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][N:12]([CH3:20])[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 24436Sodium SulfateHCID 443297Hydroxyamine hydrochlorideHCID 86690357Carbamic acid, N-[[4-(diethoxymethyl)phenyl]methyl]-N-methyl-, 1,1-dimethylethyl ester

Product 1

HCID 86690358HCID 86690358, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 73012-MethyltetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
30 °C

Procedure

A biphasic solution of tert-butyl N-[[4-(diethoxymethyl)phenyl]methyl]-N-methyl-carbamate (50.0 g, 154.6 mmol) in 2-MeTHF (400.0 mL) and Na2SO4 (100.0 mL of 10% w/v, 70.40 mmol) was stirred at 8-10° C. in a 1-L, glass-jacketed reactor. Hydroxylamine hydrochloride (46.38 mL of 5.0 M, 231.9 mmol) was added and the biphasic solution was stirred at 30° C. for 16 hours. The reaction was diluted with MTBE (200.0 mL) and the layers separated. The organic phase was washed with water (200.0 mL), dried (Na2SO4), filtered and concentrated in vacuo. The residue was diluted with heptane (200.0 mL) and the resultant suspension was stirred at ambient temperature for 30 minutes. The solid was collected by filtration to give the title compound as a white solid (36.5 g, 89% Yield); 1H NMR (400 MHz, CDCl3) δ 1.50 (s, 9H), 2.88 (br s, 3H), 4.60 (s, 2H), 7.26 (d, 2H), 7.52 (d, 2H) and 8.15 (s, 1H) ppm.

Workup

  1. customthe layers separated
  2. washThe organic phase was washed with water (200.0 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. additionThe residue was diluted with heptane (200.0 mL)
  7. stirringthe resultant suspension was stirred at ambient temperature for 30 minutes
  8. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-828aabd83caf4b2186b7d496639c5293
Source dataset
uspto-grants-2015_05
Patent number
US09035053B2

Reaction notes

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