Sodium Hydroxide → HCID 22113230, compound

HRID 1900022Notes

Reaction equation

HRID 1900022 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[C:5]([N:7]([CH2:12][CH2:13][O:14][CH3:15])[CH2:8][CH2:9][O:10][CH3:11])=[O:6].[OH-].[Na+].Cl[C:22]([O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:23]>O1CCOCC1>[CH3:15][O:14][CH2:13][CH2:12][N:7]([CH2:8][CH2:9][O:10][CH3:11])[C:5]([C:4]1[CH:3]=[C:2]([NH:1][C:22](=[O:23])[O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:18]=[CH:17][CH:16]=1)=[O:6]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 15891Phenyl chloroformateHCID 22113167HCID 22113167, compound

Product 1

HCID 22113230HCID 22113230, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 3-amino-N,N-bis(2-methoxyethyl)benzamide (1.01 g) in 1,4-dioxane (10 ml) was added 1N sodium hydroxide solution (5.2 ml) and phenyl chloroformate (0.55 ml) successively in an ice-cooled bath. The bath was removed and the reaction mixture was stirred vigorously for 1 hour, during which time phenyl chloroformate (0.25 ml) was further added. The mixture was extracted with dichloromethane and the organic layer was washed with water twice and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was crystallized from diisopropyl ether to give phenyl 3-[N,N-bis(2-methoxyethyl)carbamoyl]phenylcarbamate (1.30 g) as a colorless powder.

Workup

  1. temperaturecooled bath
  2. customThe bath was removed
  3. additionwas further added
  4. extractionThe mixture was extracted with dichloromethane
  5. washthe organic layer was washed with water twice
  6. dry with materialbrine, dried over anhydrous magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-a04d10305b284a5fb7742a70ee48acc9
Source dataset
uspto-grants-1996_11
Patent number
US05574042

Reaction notes

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