2-(4-Isocyanatophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → N-[2-Methoxy-4-(trifluoromethyl)phenyl]-N′-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]urea

HRID 1677637Notes

Reaction equation

HRID 1677637 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:4]=1[NH2:5].[N:14]([C:17]1[CH:22]=[CH:21][C:20]([B:23]2[O:27][C:26]([CH3:29])([CH3:28])[C:25]([CH3:31])([CH3:30])[O:24]2)=[CH:19][CH:18]=1)=[C:15]=[O:16]>CN(C)C1C=CN=CC=1.O1CCCC1.C(N(CC)CC)C.CO>[CH3:1][O:2][C:3]1[CH:9]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:7]=[CH:6][C:4]=1[NH:5][C:15]([NH:14][C:17]1[CH:18]=[CH:19][C:20]([B:23]2[O:27][C:26]([CH3:29])([CH3:28])[C:25]([CH3:31])([CH3:30])[O:24]2)=[CH:21][CH:22]=1)=[O:16]

Participants

7

Reactant 2

HCID 27734742-(4-Isocyanatophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 51615412-Methoxy-4-(trifluoromethyl)aniline

Product 1

HCID 67329437N-[2-Methoxy-4-(trifluoromethyl)phenyl]-N′-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ureaYield 20.6%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 1 g of 2-methoxy-4-(trifluoromethyl)aniline and 128 mg of 4-dimethylaminopyridine in 150 mL of tetrahydrofuran and 1.5 mL of triethylamine are added, at 20° C., 1.28 g of 2-(4-isocyanatophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. After 4 hours, the reaction is evaporated to dryness under reduced pressure. The residue is taken up in a mixture of ethyl acetate and water. The organic phase is dried over magnesium sulfate and then concentrated under reduced pressure. The residual yellow oil is purified on a prepacked Biotage KP-Sil column of 60 Å SiO2 32-63 μm (eluent: 8/2 cyclohexane/ethyl acetate). A pale yellow powder is obtained, which is taken up in methanol. An insoluble white material is formed, which is separated out by filtration, and the filtrate is then evaporated to dryness under reduced pressure to give 0.47 g of a pale yellow powder of 1-(2-methoxy-4-trifluoromethylphenyl)-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]urea.

Workup

  1. customthe reaction is evaporated to dryness under reduced pressure
  2. additionThe residue is taken up in a mixture of ethyl acetate and water
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residual yellow oil is purified on a prepacked Biotage KP-Sil column of 60 Å SiO2 32-63 μm (eluent: 8/2 cyclohexane/ethyl acetate)
  6. customA pale yellow powder is obtained
  7. customAn insoluble white material is formed
  8. customwhich is separated out by filtration
  9. customthe filtrate is then evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-9f9fc2dfca574b15a1eb06e971a72a91
Source dataset
uspto-grants-2011_08
Patent number
US08008322B2

Reaction notes

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