Diethyl Ether → HCID 19967409, compound

HRID 976635Notes

Reaction equation

HRID 976635 reaction equation
Cl.[CH:2]([NH:5][OH:6])([CH3:4])[CH3:3].C(OCC)C.[OH-].[Na+].[CH3:14][O:15][C:16]1[CH:17]=[C:18]([N:26]=[C:27]=[O:28])[CH:19]=[C:20]([O:24][CH3:25])[C:21]=1[O:22][CH3:23]>O>[OH:6][N:5]([CH:2]([CH3:4])[CH3:3])[C:27]([NH:26][C:18]1[CH:17]=[C:16]([O:15][CH3:14])[C:21]([O:22][CH3:23])=[C:20]([O:24][CH3:25])[CH:19]=1)=[O:28]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 170873N-Isopropylhydroxylamine HydrochlorideHCID 5177665-Isocyanato-1,2,3-trimethoxybenzene

Product 1

HCID 19967409HCID 19967409, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of N-isopropylhydroxylamine hydrochloride (1.2 g, 11 mmol) in water (5 mL) was combined with diethyl ether (35 mL) then cooled in an ice bath. A solution of sodium hydroxide (0.5 g, 12.5 mmol) in water (7 mL) was added over a 10 minute period. The reaction mixture was stirred for 10 minutes then 3,4,5-trimethoxyphenyl isocyanate (2.1 g, 10 mmol) was added as a solid. The reaction mixture was stirred at ambient temperature for 18 hours then filtered to remove a white precipitate. The filtrate was concentrated under vacuum to provide 2.1 g of the desired product as a white solid. An analytical sample was prepared by recrystallization from hexanes:ethyl acetate, m.p. 140.0°-141.0 ° C. Analysis: Calculated for C13H20N2O5 : %C, 54.92; %H, 7.09; %N, 9.85; Found: %C, 55.12; %H, 7.06; %N, 9.77.

Workup

  1. temperaturethen cooled in an ice bath
  2. stirringThe reaction mixture was stirred at ambient temperature for 18 hours
  3. filtrationthen filtered
  4. customto remove a white precipitate
  5. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-9e3da4efb6b549f292fb265acaff1240
Source dataset
uspto-grants-1997_03
Patent number
US05612377

Reaction notes

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