Water → HCID 21881984, compound

HRID 721981Notes

Reaction equation

HRID 721981 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[O:9][CH3:10].[Br:11][CH:12]([CH2:16][CH2:17]Br)[C:13](Cl)=[O:14].C(N(CC)CC)C.O>C(Cl)Cl>[Br:11][CH:12]1[CH2:16][CH2:17][N:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([O:9][CH3:10])[CH:4]=2)[C:13]1=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 44131432,4-Dibromobutyryl chlorideHCID 131036924-Chloro-3-methoxyaniline

Product 1

HCID 21881984HCID 21881984, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-chloro-3-methoxybenzeneamine (4.7 g, 29.6 mmol) in methylene chloride (100 mL) at ˜0° C. was slowly added 2,4dibromobutyryl chloride (5.1 mL, 39 mmol). After the addition, the reaction mixture was stirred for ˜5 minutes and triethylamine (24.7 mL, 178 mmol) was then added. The resulting reaction mixture was allowed to warm up to room temperature and stirred at room temperature for 5 days. Water (˜100 mL) was then added to the reaction mixture. The organic layer was separated, dried over MgSO4 and concentrated. The residue was purified by column chromatography (silica gel, ˜33% ethyl acetate/˜67% hexanes) to give the title compound as a yellow solid (3.9 g) melting at 113–115° C.

Workup

  1. customat ˜0° C.
  2. additionAfter the addition
  3. customThe resulting reaction mixture
  4. stirringstirred at room temperature for 5 days
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography (silica gel, ˜33% ethyl acetate/˜67% hexanes)

Sources & evidence

ORD record
ord-68e57b90a98b4ef38f843c4403c6a98a
Source dataset
uspto-grants-2006_11
Patent number
US07138361B2

Reaction notes

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