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Triethylamine → HCID 21867225, compound

HRID 857159
Notes
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Reaction equation

HRID 857159 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH2:4][C:5]1[CH:10]=[C:9]([Cl:11])[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:15][CH:14]=2)=[C:7]([Cl:27])[CH:6]=1.C(N(CC)CC)C.[C:36](Cl)(=[O:40])[CH:37]([CH3:39])[CH3:38]>ClCCl>[CH3:1][O:2][C:3](=[O:28])[CH2:4][C:5]1[CH:10]=[C:9]([Cl:11])[C:8]([O:12][C:13]2[CH:14]=[CH:15][C:16]([N:19]([C:36](=[O:40])[CH:37]([CH3:39])[CH3:38])[CH2:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[CH:17][CH:18]=2)=[C:7]([Cl:27])[CH:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 21867255Methyl[3,5-dichloro-4-(4-benzylaminophenoxy)phenyl]acetate

Product 1

HCID 21867225HCID 21867225, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of methyl[3,5-dichloro-4-(4-benzylaminophenoxy)phenyl]acetate (0.36 g), triethylamine (0.10 g) and dichloromethane (40 mL) was added isobutyryl chloride (0.15 g). After 16 hours at room temperature, the reaction mixture was concentrated, and the residue partioned between ethyl acetate and water. The organic phase was washed with hydrochloric acid (1 N), a saturated aqueous solution of sodium hydrogencarbonate and brine. After concentration, the residue was purified on column (silica gel, petrolium ether/ethyl acetate, 4:1) to give, to give 0.40 g of methyl[3,5-dichloro-4-(4-(2-methylpropanoyl-benzylamino)phenoxy)phenyl]acetate.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. washThe organic phase was washed with hydrochloric acid (1 N)
  3. concentrationAfter concentration
  4. customthe residue was purified on column (silica gel, petrolium ether/ethyl acetate, 4:1)
  5. customto give

Sources & evidence

ORD record
ord-9ab1c2dfbffe470dbb877b766a4f2d38
Source dataset
uspto-grants-2006_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07144909B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes