Dimethylamine → HCID 13920677, compound

HRID 2166168Notes

Reaction equation

HRID 2166168 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-80b1dc4e44f94140a713f2d53d4f3ada
Source dataset
uspto-grants-1990_07
Patent number
US04943591

Reaction notes

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