phenyl N-(2,4-difluorophenyl)carbamate → HCID 15137704, compound

HRID 359986Notes

Reaction equation

HRID 359986 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:19])=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].C1([O:26][C:27](=O)[NH:28][C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:30]=2[F:36])C=CC=CC=1>C1(C)C=CC=CC=1>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:11][N:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:19])[C:27]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:30]=2[F:36])=[O:26])=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 13733129phenyl N-(2,4-difluorophenyl)carbamateHCID 15137694HCID 15137694, compound

Product 1

HCID 15137704HCID 15137704, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1.58 g of 6-[[(4-butylphenyl)methyl]amino]-1-hexanol and 1.5 g of phenyl-N-(2,4-difluorophenyl)carbamate in 40 ml of toluene was heated at reflux for 5 hours. The reaction mixture was cooled and allowed to stand at room temperature for 16 hours. The solution was washed with 3N aqueous hydrochloric acid, brine, 1N aqueous sodium hydroxide and brine again, then was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated in vacuo and gave a yellow oil. The oil was treated by preparative high pressure liquid chromatography and gave 0.93 g (37%) of the desired product as a colorless oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 hours
  3. temperatureThe reaction mixture was cooled
  4. washThe solution was washed with 3N aqueous hydrochloric acid, brine, 1N aqueous sodium hydroxide and brine again
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customThe filtrate was evaporated in vacuo
  8. customgave a yellow oil
  9. additionThe oil was treated by preparative high pressure liquid chromatography

Sources & evidence

ORD record
ord-9e56647fd3074b7eb818075521754e3b
Source dataset
uspto-grants-1991_03
Patent number
US05003106

Reaction notes

Loading…