1-(4-Amino-3,5-dichlorophenyl)-2-bromoethan-1-one → HCID 23045282, compound

HRID 2108131Notes

Reaction equation

HRID 2108131 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([C:9](=[O:12])[CH2:10]Br)=[CH:4][C:3]=1[Cl:13].[C:14]1([CH2:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][CH2:29][NH:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1COCC1>[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([CH:9]([CH2:10][N:30]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:29][CH2:28][CH2:27][O:26][CH2:25][CH2:24][O:23][CH2:22][CH2:21][CH2:20][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[OH:12])=[CH:4][C:3]=1[Cl:13]

Participants

4

Reactant 2

HCID 30158971-(4-Amino-3,5-dichlorophenyl)-2-bromoethan-1-oneHCID 23045285HCID 23045285, compound

Product 1

HCID 23045282HCID 23045282, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-[4-Amino-3,5-dichlorophenyl]-2-bromoethanone (0.86 g), N-[3-[2-(3-phenylpropoxy)ethoxy]propyl]benzenemethanamine (1 g) and DEA (0.43 g) were stirred together in THF (30 ml) at room temperature under nitrogen for 22 h. The mixture was filtered and the filtrate evaporated in vacuo. The residue was dissolved in methanol (40 ml), treated portionwise with sodium borohydride (0.31 g) at 0° C. under nitrogen, stirred at room temperature under nitrogen for 2 h, diluted with water (150 ml) and extracted with ethyl acetate (2×150 ml). The dried extract was evaporated in vacuo to give an oil. Purification by FCC eluting with System F (1:1) gave the title compound (1.22 g) as an oil. T.l.c. (System F 1:1) Rf 0.19

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated in vacuo
  3. dissolutionThe residue was dissolved in methanol (40 ml)
  4. additiontreated portionwise with sodium borohydride (0.31 g) at 0° C. under nitrogen
  5. additiondiluted with water (150 ml)
  6. extractionextracted with ethyl acetate (2×150 ml)
  7. extractionThe dried extract
  8. customwas evaporated in vacuo
  9. customto give an oil
  10. customPurification by FCC
  11. washeluting with System F (1:1)

Sources & evidence

ORD record
ord-db150cf2821e482b8e6b9c9c56628f90
Source dataset
uspto-grants-1990_06
Patent number
US04937268

Reaction notes

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