Triethylamine → HCID 59760051, compound

HRID 1879128Notes

Reaction equation

HRID 1879128 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:10]=[C:11]([CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]([CH3:26])=[C:21]([CH:25]=2)[C:22](Cl)=[O:23])[CH:12]=[CH:13][CH:14]=1.[NH2:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:30][C:29]=1[CH3:40]>ClCCl.C(#N)C>[Cl:8][C:9]1[CH:10]=[C:11]([CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]([CH3:26])=[C:21]([C:22]([NH:27][C:28]3[CH:33]=[CH:32][C:31]([CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:30][C:29]=3[CH3:40])=[O:23])[CH:25]=2)[CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 23511836HCID 23511836, compoundHCID 59760053HCID 59760053, compound

Product 1

HCID 59760051HCID 59760051, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (74 ul, 0.53 mmol, 1.5 eq) was added to a suspension of 5-{[(3-chlorophenyl)methyl]oxy}-2-methylbenzoylchloride (105 mgs, 0.36 mmol) and ethyl (4-amino-3-methylphenyl)acetate (103 mg, 0.53 mmol, 1.5 eq) in dichloromethane (5 ml). The mixture was stirred at room temperature overnight. The mixture was then diluted with acetonitrile and purified by SCX cartridge (5 g) eluting with acetonitrile. Fractions containing product were combined and evaporated to give the title compound as a yellow gum, 174 mg. MS (ES+) m/z 452 [M+H]+ (C26H2635ClNO4).

Workup

  1. custompurified by SCX cartridge (5 g)
  2. washeluting with acetonitrile
  3. additionFractions containing product
  4. customevaporated

Sources & evidence

ORD record
ord-913468b7e6774d879fec58c4a3078719
Source dataset
uspto-grants-2012_11
Patent number
US08314147B2

Reaction notes

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