Dimethylformamide → 6-[3-Chloro-5-(1-chloroethyl)-6-methoxy-2-methylphenyl]morpholin-3-one

HRID 1499945Notes

Reaction equation

HRID 1499945 reaction equation
S(Cl)([Cl:3])=O.CN(C)C=O.[Cl:10][C:11]1[C:12]([CH3:29])=[C:13]([CH:22]2[CH2:27][NH:26][C:25](=[O:28])[CH2:24][O:23]2)[C:14]([O:20][CH3:21])=[C:15]([CH:17](O)[CH3:18])[CH:16]=1>C(Cl)Cl>[Cl:10][C:11]1[C:12]([CH3:29])=[C:13]([CH:22]2[CH2:27][NH:26][C:25](=[O:28])[CH2:24][O:23]2)[C:14]([O:20][CH3:21])=[C:15]([CH:17]([Cl:3])[CH3:18])[CH:16]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 866778606-[3-Chloro-5-(1-hydroxyethyl)-6-methoxy-2-methylphenyl]morpholin-3-one

Product 1

HCID 866778616-[3-Chloro-5-(1-chloroethyl)-6-methoxy-2-methylphenyl]morpholin-3-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of thionyl chloride (15 μL, 0.21 mmol) and N,N-dimethylformamide (10.0 μL) was stirred at room temperature for 10 minutes. A solution of 6-[3-chloro-5-(1-hydroxyethyl)-6-methoxy-2-methylphenyl]morpholin-3-one (19.0 mg, 0.0634 mmol) (racemic mixture of two diastereomers from step 5) in methylene chloride (1.0 mL) was added and the mixture was stirred at room temperature overnight. The mixture was diluted with methylene chloride, washed with saturated sodium bicarbonate, water, brine, dried over sodium sulfate, filtered and concentrated to give the desired compound as a racemic mixture of two diastereomers, 19 mg, 94%. LCMS calculated for C14H17ClNO3 (M-Cl)+: m/z=282.1; found: 282.1.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. washwashed with saturated sodium bicarbonate, water, brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-33acfa218e18417096b2756f4beb0715
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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