Methyl Isocyanate → HCID 59525695, compound

HRID 385847Notes

Reaction equation

HRID 385847 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][CH:3]=1.[CH3:10][N:11]=[C:12]=[O:13].[H-].[Na+].[NH4+].[Cl-]>CN(C1C=CN=CC=1)C.C1COCC1.O>[CH3:10][NH:11][C:12](=[O:13])[O:9][CH2:8][C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([Br:1])[N:7]=1

Participants

8

Reactant 4

HCID 12228Methyl IsocyanateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 3517811(6-Bromopyridin-2-yl)methanol

Product 1

HCID 59525695HCID 59525695, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

(6-Bromopyridin-2-yl)methanol (1.5 g, 7.98 mmol) and DMAP (0.097 g, 0.798 mmol) were taken up in THF (20 mL) and cooled to 0° C. Methyl isocyanate (0.501 g, 8.78 mmol) was added before warming to room temperature and stirring overnight. The reaction mixture was cooled to 0° C. and sodium hydride (0.319 g, 7.98 mmol) was added. After 30 minutes at 0° C., water was added followed by saturated NH4Cl and the products extracted into EtOAc (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. Purification of the residue by silica gel chromatography (6-50% EtOAc-hexanes) gave the title compound as a pale yellow solid.

Workup

  1. temperaturebefore warming to room temperature
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. waitAfter 30 minutes at 0° C.
  4. extractionthe products extracted into EtOAc (2×)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification of the residue by silica gel chromatography (6-50% EtOAc-hexanes)

Sources & evidence

ORD record
ord-3744bf43d1924bebb25c213754abb500
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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