Dimethylamine → HCID 13920677, compound

HRID 1084965Notes

Reaction equation

HRID 1084965 reaction equation
[CH3:1][NH:2][CH3:3].[I:4][C:5]1[CH:15]=[CH:14][C:8]([O:9][CH2:10][C:11](Cl)=[O:12])=[CH:7][CH:6]=1>C(N(CC)CC)C>[I:4][C:5]1[CH:15]=[CH:14][C:8]([O:9][CH2:10][C:11]([N:2]([CH3:3])[CH3:1])=[O:12])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 13140640HCID 13140640, compound

Product 1

HCID 13920677HCID 13920677, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Dimethylamine (33% w/w in IMS, 5.85 ml) was added dropwise to a suspension of (4-iodophenoxy)acetyl chloride (9.49 g) in triethylamine (50 ml) at 0° under nitrogen. The suspension was stirred for 2 h at 0° and partitioned between ethyl acetate (300 ml) and 8% aqueous sodium bicarbonate (300 ml). The organic layer was dried and the solvent was evaporated to leave an oil which was purified by FCC eluting with diethyl ether to give the title compound as a white solid (3.96 g), m.p. 63°-65°.

Workup

  1. custompartitioned between ethyl acetate (300 ml) and 8% aqueous sodium bicarbonate (300 ml)
  2. customThe organic layer was dried
  3. customthe solvent was evaporated
  4. customto leave an oil which
  5. customwas purified by FCC
  6. washeluting with diethyl ether

Sources & evidence

ORD record
ord-0c47280b42b0411eb8eefe63b86646d0
Source dataset
uspto-grants-1991_04
Patent number
US05006556

Reaction notes

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