1-(4-Amino-3,5-dichlorophenyl)-2-bromoethan-1-one → HCID 23045289, compound

HRID 2108130Notes

Reaction equation

HRID 2108130 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].[O:14]([CH2:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][CH2:30][NH:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([CH:9]([CH2:10][N:31]([CH2:30][CH2:29][CH2:28][O:27][CH2:26][CH2:25][O:24][CH2:23][CH2:22][CH2:21][O:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=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 23045306HCID 23045306, compound

Product 1

HCID 23045289HCID 23045289, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-[4-Amino-3,5-dichlorophenyl]-2-bromoethanone (0.95 g), N-[3-[2-(3-phenoxypropoxy)ethoxy]propyl]benzenemethanamine (1.15 g) and DEA (0.48 g) were stirred together in THF (35 ml) at room temperature under nitrogen for 7 h. The mixture was filtered and the filtrate evaporated in vacuo. The residue was dissolved in methanol (35 ml) and treated portionwise with sodium borohydride (0.34 g), at 0° C. under nitrogen, stirred at room temperature for 18 h, diluted with water (150 ml) and the solvent evaporated in vacuo. The residue was extracted with ethyl acetate (2×150 ml), dried and evaporated in vacuo to give an oil. Purification by FCC eluting with System H (95:5:1) gave the title compound (1.30 g) as an oil. T.l.c. (System H 90:10:1) Rf 0.39

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated in vacuo
  3. dissolutionThe residue was dissolved in methanol (35 ml)
  4. additiontreated portionwise with sodium borohydride (0.34 g), at 0° C. under nitrogen
  5. additiondiluted with water (150 ml)
  6. customthe solvent evaporated in vacuo
  7. extractionThe residue was extracted with ethyl acetate (2×150 ml)
  8. customdried
  9. customevaporated in vacuo
  10. customto give an oil
  11. customPurification by FCC
  12. washeluting with System H (95:5:1)

Sources & evidence

ORD record
ord-99f4bd39155a4b3da82a905085e89576
Source dataset
uspto-grants-1990_06
Patent number
US04937268

Reaction notes

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