Citric Acid → HCID 14227207, compound

HRID 974008Notes

Reaction equation

HRID 974008 reaction equation
[CH3:1][N:2]([CH3:14])[C:3]([NH:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4].[H-].[Na+].Br[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C>[CH2:7]([O:6][N:5]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:3]([N:2]([CH3:14])[CH3:1])=[O:4])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 81401-BromooctaneHCID 24758Sodium hydrideHCID 13547276HCID 13547276, compound

Product 1

HCID 14227207HCID 14227207, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of this urea (1.59 g, 8.19 mmol) in DMF (13 ml) at 50° C. under nitrogen was added sodium hydride (360 mg of a 60% dispersion in oil). The resulting solution was stirred for 45 minutes, and 1-bromooctane (1.83 ml) was added. After 16 hours, the mixture was poured into 1% aqueous citric acid (75 ml) and extracted 3 times with 1:1 hexane-ether. The combined extracts were dried (MgSO4), filtered, and evaporated. Purification by chromatography on silica provided N-benzyloxy-N-octyl-N',N'-dimethylurea as a colorless oil (2.04 g, 81% yield). Hydrogenolysis as in Example 2 above, and recrystallization from hexane at -40° C., provided the title compound as a white solid (875 mg, 57% yield), mp 29°-30° C.

Workup

  1. waitAfter 16 hours
  2. extractionextracted 3 times with 1:1 hexane-ether
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by chromatography on silica

Sources & evidence

ORD record
ord-5ce51c25f50b40779a12db3ed35bb92e
Source dataset
uspto-grants-1991_11
Patent number
US05066658

Reaction notes

Loading…