Water → HCID 19603375, compound

HRID 1604529Notes

Reaction equation

HRID 1604529 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:20])[NH:18][CH3:19])=[CH:13][CH:12]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[C:21]([O:25][C:26](=[O:29])[CH2:27]Br)([CH3:24])([CH3:23])[CH3:22].O>CN(C)C=O>[C:3]([O:7][C:8]([N:10]([CH2:27][C:26]([O:25][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:29])[C:11]1[CH:12]=[CH:13][C:14]([C:17](=[O:20])[NH:18][CH3:19])=[CH:15][CH:16]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 19603378HCID 19603378, compound

Product 1

HCID 19603375HCID 19603375, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil, 41.9 mg) was added to a solution of N-(tert-butoxycarbonyl)-4-methylcarbamoylaniline (250 mg) in dimethylformamide (2.5 ml) in ice water bath under nitrogen and stirred for 30 minutes under same condition. To the mixture was added tert-butylbromoacetate (234 mg) and stirred at ambient temperature for 20 hours. The reaction mixture was poured into water and extracted with chloroform. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was recrystallized from ethyl acetate--n-hexane to give N-(tert-butoxycarbonyl)-N-(tert-butoxycarbonylmethyl)-4-methylcarbamoylaniline (280 mg).

Workup

  1. stirringstirred at ambient temperature for 20 hours
  2. extractionextracted with chloroform
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-cc4e42aa5c584e72b8c74a67cba444fb
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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