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Dichloromethane → Tert-butyl 2-(4-(4-((2,4-dichlorophenethyl)carbamoyl)phenoxy)-3-cyanophenyl)propanoate

HRID 453553
Notes
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Reaction equation

HRID 453553 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]([CH3:18])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]=[CH:7][C:8]=1F)#[N:2].[Cl:19][C:20]1[CH:37]=[CH:36][C:23]([CH2:24][CH2:25][NH:26][C:27](=[O:35])[C:28]2[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=2)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:44]CCl>CS(C)=O>[Cl:44][C:22]1[CH:21]=[C:20]([Cl:19])[CH:37]=[CH:36][C:23]=1[CH2:24][CH2:25][NH:26][C:27]([C:28]1[CH:33]=[CH:32][C:31]([O:34][C:8]2[CH:7]=[CH:6][C:5]([CH:10]([CH3:18])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:4][C:3]=2[C:1]#[N:2])=[CH:30][CH:29]=1)=[O:35]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 60628097N-(4-chlorophenethyl)-4-hydroxybenzamideHCID 68467119Tert-butyl 2-(3-cyano-4-fluorophenyl)propanoate

Product 1

HCID 68466062Tert-butyl 2-(4-(4-((2,4-dichlorophenethyl)carbamoyl)phenoxy)-3-cyanophenyl)propanoate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
95 °C

Procedure

A flask was charged with tert-butyl 2-(3-cyano-4-fluorophenyl)propanoate (0.07 g), N-(4-chlorophenethyl)-4-hydroxybenzamide (0.105 g), and potassium carbonate (0.047 g) in 1 ml of DMSO and stirred at 95° C. for one day. The reaction was taken up in dichloromethane and washed with water. The organic layer was collected, dried over MgSO4, filtered, and concentrated. The crude material was purified by silica gel chromatography, eluting with a solvent system of 5%-80% ethyl acetate/hexanes gave tert-butyl 2-(4-(4-((2,4-dichlorophenethyl)carbamoyl)phenoxy)-3-cyanophenyl)propanoate (0.102 g).

Workup

  1. washwashed with water
  2. customThe organic layer was collected
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by silica gel chromatography
  7. washeluting with a solvent system of 5%-80% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-5b81197b8d634a7cbf4712bfae5cada5
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08492437B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes