Hexane → HCID 19815509, compound

HRID 465996Notes

Reaction equation

HRID 465996 reaction equation
[CH3:1][CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[NH:13][C:14]([NH:16][O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:15])[CH3:3].CCCCCC.[H-].[Na+].Br[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]>CN(C)C=O.O>[CH3:12][CH:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([CH:2]([CH3:1])[CH3:3])[C:5]=1[NH:13][C:14](=[O:15])[N:16]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:11]

Participants

7

Reactant 4

HCID 8058HexaneHCID 81731-BromodecaneHCID 24758Sodium hydrideHCID 19815508HCID 19815508, compound

Product 1

HCID 19815509HCID 19815509, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of N-[2,6-bis(1-methylethyl)phenyl]-N'-(phenylmethoxy)-urea (1.62 g, 5 mmol) in 5 ml of dry dimethylformamide is added dropwise to a room temperature suspension of hexane washed sodium hydride (0.13 g, 5.5 mmol) in 3 ml of dry dimethylformamide with stirring. When gas evolution is complete, the suspension is warmed to 60° C. and 1-bromodecane (1 ml, 5 mmol) is added dropwise. The mixture is stirred for 30 minutes, cooled to room temperature, poured into water and extracted with diethyl ether. The diethyl ether extract is diluted with hexane and washed with water, dried, filtered, and evaporated to provide a colorless solid which is triturated with hexane to give 1.47 g of N'-[2,6-bis(1-methylethyl)phenyl]-N-decyl-N-(phenylmethoxy)-urea; mp 91°-93° C.

Workup

  1. stirringThe mixture is stirred for 30 minutes
  2. temperaturecooled to room temperature
  3. extractionextracted with diethyl ether
  4. extractionThe diethyl ether extract
  5. additionis diluted with hexane
  6. washwashed with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customto provide a colorless solid which
  11. customis triturated with hexane

Sources & evidence

ORD record
ord-2349b8fd2eb04b69a84a2aa2d748f390
Source dataset
uspto-grants-1992_10
Patent number
US05155127

Reaction notes

Loading…