Methanol → HCID 10773686, compound

HRID 2066447Notes

Reaction equation

HRID 2066447 reaction equation
[CH2:1]([N:8]=[C:9]=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:11][NH:12][NH2:13].CO>C(Cl)(Cl)Cl.Cl>[CH2:1]([NH:8][C:9](=[O:10])[N:12]([CH3:11])[NH2:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 6061MethylhydrazineHCID 76639Benzyl isocyanate

Product 1

HCID 10773686HCID 10773686, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6212ChloroformSolvent2×

Procedure

A solution of Benzyl isocyanate (1.85 mL, 15.0 mmol) in 7.5 mL of CHCl3 was treated with methyl hydrazine (795 μL, 15.0 mmol) at 0° C. and stirred at the same temperature for 2 h. The resulting mixture was dissolved in 1N HCl (200 mL) and the solution was washed with CHCl3 (50 mL×3). The aqueous phase was adjusted to pH 12 with 2 M NaOHaq and then extracted with CHCl3 (100 mL×3). The organic phase was dried over Na2SO4 and concentrated in vacuo. The residue was recrystallized from hexane-CHCl3 to afford (1.7 g, 9.5 mmol, 63%) as a colorless crystal. Rf=0.44 (CHCl3:MeOH=9:1); 1H NMR (400 MHz, DMSO-d6) δ 7.28-7.19 (5H, m), 4.47 (2H, s), 4.20 (2H, d, J=6.3 Hz), 2.96 (3H, s); 13C NMR (99.5 MHz, DMSO-d6) δ 159.3, 141.1, 128.1, 127.1, 126.5, 43.1, 37.8; LC/MS [ESI+] (m/z) 180.3 (M+1)+.

Workup

  1. washthe solution was washed with CHCl3 (50 mL×3)
  2. extractionextracted with CHCl3 (100 mL×3)
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was recrystallized from hexane-CHCl3
  6. customto afford (1.7 g, 9.5 mmol, 63%) as a colorless crystal

Sources & evidence

ORD record
ord-b153a973ca6f4576858e6c6e710c8074
Source dataset
uspto-grants-2012_10
Patent number
US08293743B2

Reaction notes

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