Triethylamine → HCID 897936, compound

HRID 1956742Notes

Reaction equation

HRID 1956742 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH2:10])=[CH:5][CH:4]=1.C(N(CC)CC)C.Cl[C:19]([O:21][CH2:22][CH3:23])=[O:20].[Cl-].[NH4+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH:10][C:19](=[O:20])[O:21][CH2:22][CH3:23])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 25517Ammonium ChlorideHCID 754524-Methoxybenzylamine

Product 1

HCID 897936HCID 897936, compoundYield 43.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred solution of 6.0 mL (0.046 mole) of 4-methoxyphenylmethyl-amine and 6.5 mL (0.047 mole) of triethylamine in 200 mL of tetrahydrofuran was cooled to about 5° C., and a solution of 4.4 mL (0.046 mole) of ethyl chloroformate in 10 mL of tetrahydrofuran was added. Upon completion of the addition the reaction mixture was allowed to warm to ambient temperature, then was poured into a mixture of 200 mL of ice and 200 mL of an aqueous solution saturated with ammonium chloride. This mixture was extracted with 300 mL of diethyl ether, and the extract was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 4.2 grams (43.8% yield) of ethyl (4-methoxyphenylmethyl)-carbamate. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of the addition the reaction mixture
  2. extractionThis mixture was extracted with 300 mL of diethyl ether
  3. dry with materialthe extract was dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-312bdb6990a24a2ab3eef9083b7dd8f1
Source dataset
uspto-grants-1998_07
Patent number
US05780630

Reaction notes

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