Dichloromethane → HCID 58121137, compound

HRID 1186709Notes

Reaction equation

HRID 1186709 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]([C:17]1[CH:22]=[C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:20]([C:29]([O-:31])=[O:30])=[CH:19][CH:18]=1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:32](Cl)Cl>>[CH:6]1[C:7]2[C:15]([C:17]3[CH:22]=[C:21]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:20]([C:29]([O:31][CH3:32])=[O:30])=[CH:19][CH:18]=3)=[N:14][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[O:1][C:2]=2[CH:3]=[CH:4][CH:5]=1

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 86650347HCID 86650347, compound

Product 1

HCID 58121137HCID 58121137, compoundYield 78%

Conditions

Temperature
110 °C

Procedure

To a stirring solution of methyl 5-(2-phenoxyphenylcarbamoyl)biphenyl-2-carboxylate 102 (0.723 g, 1.7 mmol) in DCM (3 mL) was added PPA (40 g, 1.7 mmol). The reaction was heated to slowly distill off the DCM then stirred at 110° C. for 1 h. The reaction mixture was cooled to room temperature, poured into ice water then extracted with DCM. The combined organic layers were washed with water, dried over Na2SO4, filtered and solvent evaporated to provide 103 as a yellow solid (0.537 g, 78% yield) after purification by ISCO (5 to 30% ethyl acetate in hexane).

Workup

  1. temperatureThe reaction was heated
  2. distillationto slowly distill off the DCM
  3. temperatureThe reaction mixture was cooled to room temperature
  4. additionpoured into ice water
  5. extractionthen extracted with DCM
  6. washThe combined organic layers were washed with water
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customsolvent evaporated

Sources & evidence

ORD record
ord-71c71687f71a4f749aa84cd737216da8
Source dataset
uspto-grants-2014_03
Patent number
US08673911B2

Reaction notes

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