2-(4-Isocyanatophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 3-Methyl-1-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]urea

HRID 1665568Notes

Reaction equation

HRID 1665568 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([B:10]2[O:14][C:13]([CH3:16])([CH3:15])[C:12]([CH3:18])([CH3:17])[O:11]2)=[CH:6][CH:5]=1)=[C:2]=[O:3].[CH3:19][NH2:20].C1COCC1>C1COCC1>[CH3:19][NH:20][C:2]([NH:1][C:4]1[CH:9]=[CH:8][C:7]([B:10]2[O:14][C:13]([CH3:16])([CH3:15])[C:12]([CH3:18])([CH3:17])[O:11]2)=[CH:6][CH:5]=1)=[O:3]

Participants

4

Reactant 2

HCID 27734742-(4-Isocyanatophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 66615946Methylamine tetrahydrofuran

Product 1

HCID 177502733-Methyl-1-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ureaYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(4-isocyanatophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (750 mg, 3.06 mmol), 2.0M Methylamine/THF (2.3 mL, 4.60 mmol) in 50 mL of THF was stirred at room temperature for 6 hr. Then the traction mixture was concentrated to give 1-methyl-3-[4-(4, 4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-urea. (760 mg, 90% yield). Rt=2.21 min; 277 [M+H].

Workup

  1. concentrationThen the traction mixture was concentrated

Sources & evidence

ORD record
ord-29391e06981e4c51acf5bcc9a7672879
Source dataset
uspto-grants-2011_10
Patent number
US08039469B2

Reaction notes

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