Toluene → Benzyl hydrogen (2-nitrophenyl)carbonimidate

HRID 987205Notes

Reaction equation

HRID 987205 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=1[NH2:8])([O-:5])=[O:4].C1(C)C=CC=CC=1.[CH2:20]([O:27][C:28](Cl)=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O1CCCC1.O>[CH2:20]([O:27][C:28]([NH:8][C:7]1[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=1[N+:3]([O-:5])=[O:4])=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 69462-NitroanilineHCID 10387Benzyl chloroformateHCID 24758Sodium hydride

Product 1

HCID 298752Benzyl hydrogen (2-nitrophenyl)carbonimidate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

1.89 g of sodium hydride (60% content) was suspended in 23.76 g of tetrahydrofuran and cooled with ice. To the obtained suspension, 23.1 g of a tetrahydrofuran solution containing 3.00 g of 2-nitroaniline was dropwise added over 1 hr, stirred for 10 minutes, allowed to stand at room temperature and stirred for 30 minutes. To the obtained mixture, 11.12 g of a 33% toluene solution containing benzyloxycarbonyl chloride was added dropwise over 1 hr at room temperature and stirred for 2 hours. To the reaction mixture, water was added at room temperature and extracted, and separated. The obtained organic layer was washed with water and analyzed by high performance liquid chromatography to find the yield of the desired product was 90%.

Workup

  1. temperaturecooled with ice
  2. additionwas dropwise added over 1 hr
  3. customto stand at room temperature
  4. stirringstirred for 30 minutes
  5. additionwas added dropwise over 1 hr at room temperature
  6. stirringstirred for 2 hours
  7. extractionextracted
  8. customseparated
  9. washThe obtained organic layer was washed with water

Sources & evidence

ORD record
ord-2ee89195011241e6804daed75a73b1f0
Source dataset
uspto-grants-2003_10
Patent number
US06630598B2

Reaction notes

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