Methyl chloroformate → HCID 67533511, compound

HRID 1879028Notes

Reaction equation

HRID 1879028 reaction equation
[F:1][C:2]1[C:7]([S:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:10]1[CH2:11][CH2:12][NH:13][CH2:14][CH:15]=1.C(N(CC)CC)C.Cl[C:24]([O:26][CH3:27])=[O:25]>C(Cl)Cl>[F:1][C:2]1[C:7]([S:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:10]1[CH2:15][CH2:14][N:13]([C:24]([O:26][CH3:27])=[O:25])[CH2:12][CH:11]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 57448065HCID 57448065, compound

Product 1

HCID 67533511HCID 67533511, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 4-[2-fluoro-3-(methylthio)phenyl]-1,2,3,6-tetrahydropyridine (1.35 g, 6.05 mmol) and triethyl amine (1.2 ml, 7.2 mmol) in methylen chloride (20 ml) at 0° C., a solution of methyl chloroformate (0.49 g, 6.6 mmol) in methylen chloride (5 ml), was added dropwise. The mixture was stirred for 15 min at 0° C. and for 1 h at ambient temperature. The reaction was quenched with aqueous sodium carbonate (10%, 50 ml), the phases were separated and the aqueous phase was extracted with methylen chloride (3×50 ml). The combined organic phases was dried (MgSO4), filtered and evaporated to dryness to give the title compound (0.95 g). MS m/z (rel. intensity, 70 eV) 281 (M+, 65), 267 (16), 266 (bp), 147 (27), 146 (25).

Workup

  1. customThe reaction was quenched with aqueous sodium carbonate (10%, 50 ml)
  2. customthe phases were separated
  3. extractionthe aqueous phase was extracted with methylen chloride (3×50 ml)
  4. dry with materialThe combined organic phases was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-fd72b68a5a144479b347157ccd8a64d5
Source dataset
uspto-grants-2012_11
Patent number
US08314126B2

Reaction notes

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