Benzene → HCID 53819833, compound

HRID 1763789Notes

Reaction equation

HRID 1763789 reaction equation
[CH2:1]([NH:7][CH2:8][CH2:9][CH:10]1[O:14][C:13]([CH3:16])([CH3:15])[C:12]([CH3:18])([CH3:17])[O:11]1)[CH2:2][CH2:3][CH:4]=[CH:5][CH3:6].C1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].Cl[C:32](=[O:37])[CH:33]([Cl:36])[CH2:34][CH3:35]>O>[CH2:1]([N:7]([CH2:8][CH2:9][CH:10]1[O:11][C:12]([CH3:17])([CH3:18])[C:13]([CH3:16])([CH3:15])[O:14]1)[C:32](=[O:37])[CH:33]([Cl:36])[CH2:34][CH3:35])[CH2:2][CH2:3][CH:4]=[CH:5][CH3:6]

Participants

6

Reactant 4

HCID 241BenzeneHCID 10340Sodium CarbonateHCID 1390532-Chlorobutanoyl chlorideHCID 54540778HCID 54540778, compound

Product 1

HCID 53819833HCID 53819833, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-Hex-4-enyl-N-(4,4,5,5-tetramethyl-1,3-dioxolan-2-ylethyl)-amine (10 grams), benzene (100 ml), water (100 ml) and sodium carbonate (8 grams) are charged into a glass reaction vessel equipped with a mechanical stirrer and thermometer. The reaction mixture is cooled to a temperature of 5° to 10° C. and α-chlorobutanoyl chloride (7 grams) is added dropwise with stirring. After the addition is completed stirring is continued until the reaction mixture reaches room temperature. After this time the organic phase is separated from the aqueous phase and is washed with water. The washed solution is then dried over anhydrous magnesium sulfate, filtered and stripped of solvent under reduced pressure to yield the desired product N-hex-4-enyl-N-(4,4,5,5-tetramethyl-1,3-dioxolan-2-ylethyl)-α-chlorobutanamide.

Workup

  1. customequipped with a mechanical stirrer
  2. additionis added dropwise
  3. additionAfter the addition
  4. stirringis completed stirring
  5. customreaches room temperature
  6. customAfter this time the organic phase is separated from the aqueous phase
  7. washis washed with water
  8. dry with materialThe washed solution is then dried over anhydrous magnesium sulfate
  9. filtrationfiltered

Sources & evidence

ORD record
ord-c283180393894e78ba02efdab8807882
Source dataset
uspto-grants-1978_09
Patent number
US04113464

Reaction notes

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