Benzyl chloroformate → benzyl N-[(4-iodophenyl)methyl]carbamate

HRID 2096286Notes

Reaction equation

HRID 2096286 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH2:9])=[CH:4][CH:3]=1.Cl[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12].C([O-])([O-])=O.[K+].[K+]>O1CCCC1.O>[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:11](=[O:12])[O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 27375334-Iodobenzylamine

Product 1

HCID 67440714benzyl N-[(4-iodophenyl)methyl]carbamate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4-iodophenyl)methanamine (5 g, 18.5 mmol) and benzyl chloroformate (3.47 g) in a mixture of tetrahydrofuran (20 mL) and H2O (50 mL) was added K2CO3 (10.2 g, 74 mmol) at 5° C. The reaction mixture was stirred at room temperature for 5 hours, and partitioned between ethyl acetate and brine. The organic phase was washed with brine, dried over MgSO4, filtered, and concentrated to afford the title compound. LC-MS (ESI): m/z 368 (M+H), RT: 2.25 min; 1H NMR (400 MHz, CDCl3): δ 4.32 (d, J=6.0 Hz, 2H), 5.13 (s, 2H), 7.03 (d, J=7.6 Hz, 2H), 7.32-7.36 (m, 5H), 7.65 (d, J=8.0 Hz, 2H).

Workup

  1. custompartitioned between ethyl acetate and brine
  2. washThe organic phase was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e3c9b67bce154b4aa76ad864209005d8
Source dataset
uspto-grants-2013_05
Patent number
US08450320B2

Reaction notes

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