Ethylamine → N-Ethyl-2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

HRID 1773661Notes

Reaction equation

HRID 1773661 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([B:11]2[O:15][C:14]([CH3:17])([CH3:16])[C:13]([CH3:19])([CH3:18])[O:12]2)[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[CH2:20]([NH2:22])[CH3:21].C(P1(=O)OP(=O)(CCC)OP(=O)(CCC)O1)CC>CN1C(=O)CCC1>[CH2:20]([NH:22][C:4](=[O:5])[C:3]1[CH:7]=[CH:8][C:9]([B:11]2[O:12][C:13]([CH3:19])([CH3:18])[C:14]([CH3:16])([CH3:17])[O:15]2)=[CH:10][C:2]=1[CH3:1])[CH3:21]

Participants

5

Reactant 3

HCID 6341EthylamineHCID 111923Propylphosphonic anhydrideHCID 532167732-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)benzoic acid

Product 1

HCID 66691208N-Ethyl-2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a stirred solution of 15 g (57 mmol) 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid in NMP (20 mL) were added 85.84 mL (171.68 mmol) ethylamine and 72.8 mL 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (114.45 mmol, 2M in THF) and the mixture was stirred for 2 h at rt to give after working up and purification 16.00 g (96.7%) of the title compound.

Workup

  1. customto give
  2. custompurification 16.00 g (96.7%) of the title compound

Sources & evidence

ORD record
ord-a637db1e75824d1fb1421f80235806d3
Source dataset
uspto-grants-2016_02
Patent number
US09255100B2

Reaction notes

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