Pyridine → HCID 57758283, compound

HRID 2198079Notes

Reaction equation

HRID 2198079 reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([CH3:3])[CH3:2].N1C=CC=CC=1.Cl[C:18]([O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19]>C1COCC1>[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH:6][C:18](=[O:19])[O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 125612-IsopropylanilineHCID 15891Phenyl chloroformate

Product 1

HCID 57758283HCID 57758283, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-isopropylaniline (200 mg, 1.5 mmol) in THF (9 mL) was added pyridine (0.24 mL, 3.0 mmol), then phenyl chloroformate (0.28 mL, 2.2 mmol) at rt. Some solid precipitated out. The mixture was stirred at rt for 4.5 h. Water was added to the reaction and it was extracted with EtOAc. The organic solution was washed with water (5 mL) and dried over MgSO4 and then filtered. The filtrate was concentrated in vacuo and crystallized from EtOAc-hexanes (1:9 v/v) to afford the title compound (130 mg, 34%). 1H-NMR (DMSO-d6) δ 9.45 (s, 1H), 7.44 to 7.36 (m, 2H), 7.35 to 7.28 (m, 2H), 7.25 to 7.14 (m, 5H), 3.27 (m, 1H), 1.17 (d, J=6.9 Hz, 2H); TLC Rf=0.33 (9:1 v/v hexanes-EtOAc).

Workup

  1. customat rt
  2. customSome solid precipitated out
  3. additionWater was added to the reaction and it
  4. extractionwas extracted with EtOAc
  5. washThe organic solution was washed with water (5 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuo
  9. customcrystallized from EtOAc-hexanes (1:9 v/v)

Sources & evidence

ORD record
ord-06cf3dd9d9684cc19cd932601a1abb03
Source dataset
uspto-grants-2012_12
Patent number
US08338595B2

Reaction notes

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