Methyl chloroformate → HCID 10858327, compound

HRID 399170Notes

Reaction equation

HRID 399170 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([O:9][CH3:10])=[CH:4][C:3]=1[CH2:11][NH2:12].C(N(CC)CC)C.Cl[C:21]([O:23][CH3:24])=[O:22]>C1COCC1>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([O:9][CH3:10])=[CH:4][C:3]=1[CH2:11][NH:12][C:21](=[O:22])[O:23][CH3:24]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 117903632,3-Dichloro-5-methoxybenzenemethanamine

Product 1

HCID 10858327HCID 10858327, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

A stirred solution of 54.0 grams (0.262 mole) of 2,3-dichloro-5-methoxy-phenylmethylamine and 27.0 grams (0.267 mole) of triethylamine in 1000 mL of THF was cooled below 5° C., and 24.8 grams (0.262 mole) of methyl chloroformate was added dropwise at a rate to maintain the reaction mixture temperature below 5° C. Upon completion of addition, the reaction mixture was stirred at about 5° C. for one hour, then it was allowed to warm to ambient temperature as it stirred for about 18 hours. After this time thin layer chromatographic (TLC) analysis of the reaction mixture indicated the reaction was complete. The reaction mixture was concentrated under reduced pressure to a residue, which was then shaken with ethyl acetate and water. The aqueous layer was washed with ethyl acetate, and the wash was combined with the original organic layer. The combination was then washed with one portion of water and one portion of an aqueous saturated sodium chloride solution. The organic layer was dried with sodium sulfate, filtered, and concentrated under reduced pressure, yielding 66.0 grams (95.3% yield) of the subject compound, mp 90°-91° C. (99% pure by gas chromatographic (GC) analysis). The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperatureto maintain the reaction mixture temperature below 5° C
  2. additionUpon completion of addition
  3. temperatureto warm to ambient temperature as it
  4. stirringstirred for about 18 hours
  5. concentrationThe reaction mixture was concentrated under reduced pressure to a residue, which
  6. stirringwas then shaken with ethyl acetate and water
  7. washThe aqueous layer was washed with ethyl acetate
  8. washThe combination was then washed with one portion of water and one portion of an aqueous saturated sodium chloride solution
  9. dry with materialThe organic layer was dried with sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b0fc62551e3640be8da30f63c6f1fd79
Source dataset
uspto-grants-1998_10
Patent number
US05817814

Reaction notes

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