4-Aminobenzonitrile → 2-(tert-butoxycarbonylamino)-N-(4-cyanophenyl)acetamide

HRID 1106488Notes

Reaction equation

HRID 1106488 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:25][C:26]1[CH:33]=[CH:32][C:29]([C:30]#[N:31])=[CH:28][CH:27]=1>O1CCCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([NH:25][C:26]1[CH:33]=[CH:32][C:29]([C:30]#[N:31])=[CH:28][CH:27]=1)=[O:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 133964-AminobenzonitrileHCID 682631,1'-CarbonyldiimidazoleHCID 78288N-(tert-butoxycarbonyl)glycine

Product 1

HCID 187889442-(tert-butoxycarbonylamino)-N-(4-cyanophenyl)acetamideYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(tert-Butoxycarbonyl)glycine (14.83 g) was dissolved in 50 ml of tetrahydrofuran, and 13.73 g of 1,1'-carbonylbis-1H-imidazole was gradually added, and the mixture was stirred at room temperature for 3 hours. Then, 10 g of p-aminobenzonitrile was added and the mixture was stirred for 3 days. Then, the solvent was removed by evaporation under a reduced pressure. Water was added to the resulting residue. The crystals thus formed were collected by filtration, washed with a small amount of ethanol, and then dried under a reduced pressure to give 20.5 g of 2-(tert-butoxycarbonylamino)-N-(4-cyanophenyl)acetamide.

Workup

  1. stirringthe mixture was stirred for 3 days
  2. customThen, the solvent was removed by evaporation under a reduced pressure
  3. additionWater was added to the resulting residue
  4. customThe crystals thus formed
  5. filtrationwere collected by filtration
  6. washwashed with a small amount of ethanol
  7. customdried under a reduced pressure

Sources & evidence

ORD record
ord-bae3bed1f7204500bac4db43b6f47996
Source dataset
uspto-grants-2000_05
Patent number
US06057324

Reaction notes

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