Methylamine → 1-Methyl-3-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea

HRID 407080Notes

Reaction equation

HRID 407080 reaction equation
[CH3:1][NH2:2].[N:3]([C:6]1[CH:7]=[C:8]([B:12]2[O:16][C:15]([CH3:18])([CH3:17])[C:14]([CH3:20])([CH3:19])[O:13]2)[CH:9]=[CH:10][CH:11]=1)=[C:4]=[O:5]>O1CCCC1.C(OCC)(=O)C>[CH3:1][NH:2][C:4]([NH:3][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([B:12]2[O:16][C:15]([CH3:18])([CH3:17])[C:14]([CH3:20])([CH3:19])[O:13]2)[CH:7]=1)=[O:5]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 441187472-(3-Isocyanatophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 108023721-Methyl-3-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl amine (2.0 M in THF) was added to a solution of 2-(3-isocyanatophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.49 g, 2.0 mmol) and in tetrahydrofuran (6.0 mL) at 0° C. The mixture was stirred at this temperature for 5 min, then at r.t. for 2 h. The mixture was diluted with ethyl acetate, washed with water, 1N HCl aq. and brine, dried over Na2SO4, filtered and concentrated under reduced pressure to provide the desired product which was directly used in next step without further purification. LCMS (M+H)+: m/z=277.1

Workup

  1. waitat r.t. for 2 h
  2. washwashed with water, 1N HCl aq. and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c7255171c07247569bd79e6d080cea7d
Source dataset
uspto-grants-2014_06
Patent number
US08754114B2

Reaction notes

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