Dichloromethane → HCID 131733156, compound

HRID 1525795Notes

Reaction equation

HRID 1525795 reaction equation
[CH2:1]([C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[C:23](=[O:26])([O-])[O-:24].[K+].[K+].Cl[CH2:30]Cl>ClC(OC)=O.O>[CH3:30][O:24][C:23](=[O:26])[NH:20][C:19]1[CH:18]=[CH:17][C:16]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 713745384-Pentadecylaniline

Product 1

HCID 131733156HCID 131733156, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6586Methyl chloroformateSolvent

Procedure

To the solution of 4-pentadecanylaniline (3.4 g) in dichloromethane (60 mL), methyl chloroformate (1.1 mL) and the solution of potassium carbonate (7.8 g) in water (110 mL) were added at 0° C., followed by stirring at room temperature for 14 hours. The reaction solution was poured to water, followed by extraction with dichloroethane. The organic layer was washed sequentially with 2N hydrochloric acid, water and an aqueous saturated sodium chloride solution, and dried with anhydrous magnesium sulfate. The reaction solution was concentrated under reduced pressure to obtain the title compound (3.9 g) having the following physical property values.

Workup

  1. extractionfollowed by extraction with dichloroethane
  2. washThe organic layer was washed sequentially with 2N hydrochloric acid, water
  3. dry with materialan aqueous saturated sodium chloride solution, and dried with anhydrous magnesium sulfate
  4. concentrationThe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-13fd395f19c3494abcaa9807e6014fc5
Source dataset
uspto-grants-2015_07
Patent number
US09085523B2

Reaction notes

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