Methyl chloroformate → Methyl[2-(2-bromophenyl)ethyl](2-ethoxyethyl)carbamate

HRID 387642Notes

Reaction equation

HRID 387642 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][NH:10][CH2:11][CH2:12][O:13][CH2:14][CH3:15].C(N(CC)CC)C.Cl[C:24]([O:26][CH3:27])=[O:25].[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C>[CH3:27][O:26][C:24](=[O:25])[N:10]([CH2:9][CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1])[CH2:11][CH2:12][O:13][CH2:14][CH3:15]

Participants

7

Reactant 4

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 684705122-(2-bromophenyl)-N-(2-ethoxyethyl)ethanamine

Product 1

HCID 68470585Methyl[2-(2-bromophenyl)ethyl](2-ethoxyethyl)carbamate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

2.45 g of 2-(2-bromophenyl)-N-(2-ethoxyethyl)ethanamine and 1.4 cm3 of triethylamine in solution in 22 cm3 of anhydrous tetrahydrofuran are stirred under an inert atmosphere at 0° C. 1.3 cm3 of methyl chloroformate in solution in 4 cm3 of tetrahydrofuran are poured into the reaction mixture. This mixture is then stirred for 20 h at a temperature close to 20° C. 50 cm3 of a saturated aqueous solution of ammonium chloride and 50 cm3 of ethyl acetate are added. After decanting, the organic phase is washed twice with 20 cm3 of water then 20 cm3 of a saturated aqueous solution of sodium chloride, it is dried over magnesium sulfate and filtered through a bed of silica of 30 g. The latter is washed twice with 75 cm3 of ethyl acetate. The filtrate is concentrated using a rotary evaporator under reduced pressure (5 kPa). 2.97 g of methyl[2-(2-bromophenyl)ethyl](2-ethoxyethyl)carbamate are obtained in the form of a yellow oil.

Workup

  1. customclose to 20° C
  2. customAfter decanting
  3. washthe organic phase is washed twice with 20 cm3 of water
  4. dry with material20 cm3 of a saturated aqueous solution of sodium chloride, it is dried over magnesium sulfate
  5. filtrationfiltered through a bed of silica of 30 g
  6. washThe latter is washed twice with 75 cm3 of ethyl acetate
  7. concentrationThe filtrate is concentrated
  8. customa rotary evaporator under reduced pressure (5 kPa)

Sources & evidence

ORD record
ord-d5c87d44866a4364bc4e2d67838d9dfb
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

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