Hydrochloric Acid → HCID 18400183, compound

HRID 376340Notes

Reaction equation

HRID 376340 reaction equation
[OH:1][C:2]([CH3:14])([CH3:13])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][CH:6]=1)=[O:4].C1CCN2C(=NCCC2)CC1.[C:26](Cl)(=[O:28])[CH3:27].Cl>CN(C1C=CN=CC=1)C.ClCCl>[CH3:13][C:2]([O:1][C:26](=[O:28])[CH3:27])([CH3:14])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][CH:6]=1)=[O:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2×HCID 114131682-Hydroxy-4'(methylthio)isobutyrophenone

Product 1

HCID 18400183HCID 18400183, compoundYield 41.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a 0° C. solution of 2-hydroxy-2-methyl-1-(4-(methylthio)phenyl)propan-1-one (150 g, example 1, Step 2), DBU (217 g) and DMAP (7 g) in dichloromethane (850 mL) was added acetyl chloride (112.2 g) dropwise and the mixture was stirred for 6 h. at 25° C. More DBU (32.5 g) was added and the mixture was stirred an additional 16 h. The reaction mixture was poured over 2N HCl (800 mL) and the organic layer was separated, washed with a saturated solution of NaHCO3, dried over MgSO4, filtered and the solvent was evaporated under vacuum. The residue was swished in Et2O, then 25% ethyl acetate in hexane, then filtered and dried giving 74 g of the title compound.

Workup

  1. stirringthe mixture was stirred an additional 16 h
  2. customthe organic layer was separated
  3. washwashed with a saturated solution of NaHCO3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent was evaporated under vacuum
  7. filtration25% ethyl acetate in hexane, then filtered
  8. customdried

Sources & evidence

ORD record
ord-0e7756f7716c4f2a85fc877efc89cbf2
Source dataset
uspto-grants-2000_02
Patent number
US06020343

Reaction notes

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