Methyl chloroformate → HCID 21831182, compound

HRID 1601146Notes

Reaction equation

HRID 1601146 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[CH3:6][C:7]1[CH:22]=[CH:21][CH:20]=[CH:19][C:8]=1[O:9][CH2:10][C:11]1[C:16]([NH:17][OH:18])=[CH:15][CH:14]=[CH:13][N:12]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[OH:18][N:17]([C:16]1[C:11]([CH2:10][O:9][C:8]2[CH:19]=[CH:20][CH:21]=[CH:22][C:7]=2[CH3:6])=[N:12][CH:13]=[CH:14][CH:15]=1)[C:2](=[O:3])[O:4][CH3:5]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 516892Sodium BicarbonateHCID 21831175HCID 21831175, compound

Product 1

HCID 21831182HCID 21831182, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

2.1 g (22 mmol) of methyl chloroformate were added dropwise at -10° C. to a mixture of 4.3 g (mmol) of N-[2-(2-methylphenoxymethyl)pyridin-3-yl]hydroxylamine (Example 3.e), 3.3 g (39 mmol) of NaHCO3 (solid) and 50 ml of methylene chloride. After the reaction mixture had been stirred for 4 hours at room temperature (approximately 25° C.), it was washed with water, dried and freed from solvent under reduced pressure. The residue was purified by column chromatography (cyclohexane/ethyl acetate). This gave 0.6 g (10%) of the title compound as a yellow oil.

Workup

  1. washwas washed with water
  2. customdried
  3. customThe residue was purified by column chromatography (cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-9d72895ddf484c85a0c550adabd33d4c
Source dataset
uspto-grants-1999_11
Patent number
US05977146

Reaction notes

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