1-Butanamine, N,N-dibutyl-, hydrochloride (1:1) → (2-Butyl-5-nitro-1-benzofuran-3-yl)(4-hydroxyphenyl)methanone

HRID 245345

Reaction equation

HRID 245345 reaction equation
[CH2:1]([C:5]1[O:6][C:7]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][C:8]=2[C:9]=1[C:10](=[O:19])[C:11]1[CH:16]=[CH:15][C:14]([O:17]C)=[CH:13][CH:12]=1)[CH2:2][CH2:3][CH3:4].Cl.C(N(CCCC)CCCC)CCC>>[CH2:1]([C:5]1[O:6][C:7]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][C:8]=2[C:9]=1[C:10](=[O:19])[C:11]1[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 805701-Butanamine, N,N-dibutyl-, hydrochloride (1:1)HCID 22595055(2-Butyl-5-nitrobenzofuran-3-yl)(4-methoxyphenyl)methanone

Product 1

HCID 11473234(2-Butyl-5-nitro-1-benzofuran-3-yl)(4-hydroxyphenyl)methanone

Procedure

1.50 g (4.25 mmol) of 2-n-butyl-3-(4-methoxybenzoyl)-5-nitrobenzofuran (Ia) were dissolved in 4.71 g (21.2 mmol) of tri-n-butylamine-hydrochloride at 150° C. After 16 h LC-MS analysis indicated the complete consumption of the starting material and the reaction mixture was cooled to room temperature. After addition of 20 ml of water and 50 ml MTBE the phases were separated, the organic layer was washed once with 25 ml of 1M HCl and 20 ml of water, dried over MgSO4 and evaporated. Flash chromatography gave the title compound which crystallized to yield 1.10 g (76%).

Workup

  1. customthe complete consumption of the starting material
  2. additionAfter addition of 20 ml of water and 50 ml MTBE the phases
  3. customwere separated
  4. washthe organic layer was washed once with 25 ml of 1M HCl and 20 ml of water
  5. dry with materialdried over MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-8f38abff3dc54b45b977ff1b4049ff33
Source dataset
uspto-grants-2014_02
Patent number
US08658808B2

Linked notes

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