Triethylamine → 4-Nitrophenyl ethyl(methyl)carbamate

HRID 918981Notes

Reaction equation

HRID 918981 reaction equation
[CH2:1]([N:3](CC)[CH2:4]C)[CH3:2].Cl[C:9]([O:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1)=[O:10].C(NC)C>CN(C=O)C>[CH2:1]([N:3]([CH3:4])[C:9](=[O:10])[O:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12219N-MethylethylamineHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 467815564-Nitrophenyl ethyl(methyl)carbamateYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethylamine (12.84 g, 127.11 mmol) and p-nitrophenyl chloroformate (63.56 mmol, 12.8 g) were added to a room temperature solution of N-ethylmethylamine (2.50 g, 42.37 mmol) in dry DMF (70 mL) under an argon atmosphere. After 2 h, the reaction mixture was quenched with water, diluted with EtOAc (200 mL), washed with water (2×100 mL), and brine (75 mL). All volatiles were removed under reduced pressure and the residue was purified by SiO2 column chromatography using 10% EtOAc/hexanes to afford compound 4-nitrophenyl ethyl(methyl)carbamate (5.8 g, 76%) as a yellow oil. TLC: 20% EtOAc/hexanes, Rf≈0.50; 1H NMR (CDCl3, 300 MHz) δ 8.18-8.21 (m, 2H), 7.25-7.29 (m, 2H), 3.37-3.46 (m, 2H), 3.05 and 2.97 (s, 3H for two rotamers in 60/40 ratio), 1.17-1.22 (m, 3H).

Workup

  1. customthe reaction mixture was quenched with water
  2. additiondiluted with EtOAc (200 mL)
  3. washwashed with water (2×100 mL), and brine (75 mL)
  4. customAll volatiles were removed under reduced pressure
  5. customthe residue was purified by SiO2 column chromatography

Sources & evidence

ORD record
ord-78deda074e8c4650b4074051e1e237be
Source dataset
uspto-grants-2016_03
Patent number
US09272991B2

Reaction notes

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