Thionyl Chloride → HCID 403394, compound

HRID 1402746Notes

Reaction equation

HRID 1402746 reaction equation
O[CH2:2][C:3]([NH:6][C:7]([C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=1)=[O:8])([CH3:5])[CH3:4].S(Cl)(Cl)=O>>[CH3:2][C:3]1([CH3:5])[CH2:4][O:8][C:7]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)=[N:6]1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 66739759HCID 66739759, compound

Product 1

HCID 403394HCID 403394, compoundYield 84%

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 4-[(2-hydroxy-1,1-dimethylethyl)carbamoyl]benzoate (100 mg, 0.40 mmol) in CDCl3 (2 mL) was added thionyl chloride (57 mg, 0.48 mmol). The mixture was heated to 60° C. in a sealed tube for 4 h. After cooling, the reaction was quenched by pouring onto saturated aqueous NaHCO3 (20 mL). After extraction with dichloromethane (3×20 mL), the combined organic extracts were washed with brine (20 mL), dried (MgSO4), filtered and concentrated at reduced pressure. Purification by silica FCC (eluting with 20:80 heptane/EtOAc) gave the title compound (78 mg, 84% yield) as colourless oil.

Workup

  1. temperatureAfter cooling
  2. customthe reaction was quenched
  3. additionby pouring onto saturated aqueous NaHCO3 (20 mL)
  4. extractionAfter extraction with dichloromethane (3×20 mL)
  5. washthe combined organic extracts were washed with brine (20 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated at reduced pressure
  9. customPurification
  10. washby silica FCC (eluting with 20:80 heptane/EtOAc)

Sources & evidence

ORD record
ord-c5c85c141da14f918433e751f16fc913
Source dataset
uspto-grants-2014_12
Patent number
US08912176B2

Reaction notes

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