4-Methylmorpholine → HCID 131729082, compound

HRID 1669901Notes

Reaction equation

HRID 1669901 reaction equation
C[S:2][C:3]1[CH:8]=[CH:7][C:6](O)=[CH:5][CH:4]=1.Cl[C:11]([O:13][CH:14]([Cl:18])[CH:15]([CH3:17])[CH3:16])=[O:12].[CH3:19]N1CCOCC1>ClCCl>[CH3:19][C:6]1[CH:7]=[CH:8][C:3]([S:2][C:11]([O:13][CH:14]([Cl:18])[CH:15]([CH3:17])[CH3:16])=[O:12])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 140864-(Methylthio)phenolHCID 27333261-Chloro-2-Methylpropyl Chloroformate

Product 1

HCID 131729082HCID 131729082, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

4-(Methylthio)phenol (28 g) and dichloromethane (100 mL) were charged to a vessel. The vessel was cooled to approximately 0° C. 1-Chloro-2-methylpropyl chloroformate (14 mL) was added. A solution of 4-methylmorpholine (24 g) in dichloromethane (100 mL) was then slowed added using an addition funnel, keeping the temperature below 15° C. The reaction mixture was then stirred at approximately 0° C. for 10 minutes. The reaction mixture was then stirred at room temperature overnight. The reaction mixture was washed with water (2×100 mL) followed by evaporation to an oil. Fifty-four grams (54 g) of the title compound D4 was obtained.

Workup

  1. customthe temperature below 15° C
  2. stirringThe reaction mixture was then stirred at room temperature overnight
  3. washThe reaction mixture was washed with water (2×100 mL)
  4. customfollowed by evaporation to an oil

Sources & evidence

ORD record
ord-58b442b1ed1944798bbc2c66f53360ab
Source dataset
uspto-grants-2011_08
Patent number
US07989641B2

Reaction notes

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