Tetrahydrofuran → N-(3,3-dichloro-1-ethyl-1-methyl-2-oxopropyl)-4-diethylaminobenzamide

HRID 583140Notes

Reaction equation

HRID 583140 reaction equation
[CH2:1]([N:3]([CH2:13][CH3:14])[C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=1)[CH3:2].O1CCCC1.CS(Cl)(=O)=O.Cl.[NH2:26][C:27]([CH3:35])([CH2:33][CH3:34])[C:28](=[O:32])[CH:29]([Cl:31])[Cl:30]>C(OCC)(=O)C.O.C(N(CC)CC)C>[Cl:30][CH:29]([Cl:31])[C:28](=[O:32])[C:27]([NH:26][C:8](=[O:10])[C:7]1[CH:6]=[CH:5][C:4]([N:3]([CH2:1][CH3:2])[CH2:13][CH3:14])=[CH:12][CH:11]=1)([CH2:33][CH3:34])[CH3:35]

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 31297Methanesulfonyl chlorideHCID 79480Benzoic acid, 4-(diethylamino)-HCID 183720063-Amino-1,1-dichloro-3-methyl-2-pentanone hydrochloride

Product 1

HCID 17760243N-(3,3-dichloro-1-ethyl-1-methyl-2-oxopropyl)-4-diethylaminobenzamideYield 7.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a 250 mL three-necked, round-bottomed flask fitted with a mechanical stirrer nitrogen inlet and thermometer were placed 3 g of 4-diethylaminobenzoic acid, 60 mL of tetrahydrofuran and 6.4 g of triethylamine. To the resulting well-stirred mixture was added 1.3 mL methane sulfonyl chloride dropwise while keeping the reaction temperature at -30° C. The resulting suspension was stirred at -30° C. for 15 minutes, after which 3.76 g of 3-amino-1,1-dichloro-3-methyl-2-pentanone hydrochloride were added slowly over a 60 minute period. After the addition was completed, the reaction mixture was stirred at -30° C. for an additional 45 minutes. The reaction mixture was poured into a mixture of 200 mL of water and 100 mL of ethyl acetate. The phases were separated and the aqueous layer was extracted with ethyl acetate (2×60 mL). The combined organic phases were washed sequentially with water (1×60 mL), 3% aqueous hydrochloric acid (2×100 mL), brine (1×100 mL) and 3% aqueous sodium hydroxide (2×100 mL), and then dried over anhydrous magnesium sulfate. The solvent then was removed using a rotary evaporator, yielding 410 mg N-(3,3-dichloro-1-ethyl-1-methyl-2-oxopropyl)-4-diethylaminobenzamide.

Workup

  1. customIn a 250 mL three-necked, round-bottomed flask fitted with a mechanical stirrer nitrogen inlet
  2. customat -30° C
  3. stirringThe resulting suspension was stirred at -30° C. for 15 minutes
  4. additionAfter the addition
  5. stirringthe reaction mixture was stirred at -30° C. for an additional 45 minutes
  6. customThe phases were separated
  7. extractionthe aqueous layer was extracted with ethyl acetate (2×60 mL)
  8. washThe combined organic phases were washed sequentially with water (1×60 mL), 3% aqueous hydrochloric acid (2×100 mL), brine (1×100 mL) and 3% aqueous sodium hydroxide (2×100 mL)
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customThe solvent then was removed
  11. customa rotary evaporator

Sources & evidence

ORD record
ord-d2d8751c856b4edfada55cf8f42060e8
Source dataset
uspto-grants-1999_07
Patent number
US05929098

Reaction notes

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