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Benzene → N-(2,2-dipropoxyethyl)-N-(4-methyl-1,3-dioxan-2-ylmethyl)-alpha-chloroacetamide

HRID 839817
Notes
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Reaction equation

HRID 839817 reaction equation
[CH2:1]([O:4][CH:5]([O:16][CH2:17][CH2:18][CH3:19])[CH2:6][NH:7][CH2:8][CH:9]1[O:14][CH:13]([CH3:15])[CH2:12][CH2:11][O:10]1)[CH2:2][CH3:3].C1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl:32][CH2:33][C:34](Cl)=[O:35]>O>[CH2:17]([O:16][CH:5]([O:4][CH2:1][CH2:2][CH3:3])[CH2:6][N:7]([CH2:8][CH:9]1[O:14][CH:13]([CH3:15])[CH2:12][CH2:11][O:10]1)[C:34](=[O:35])[CH2:33][Cl:32])[CH2:18][CH3:19]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 241BenzeneHCID 6577Chloroacetyl chlorideHCID 10340Sodium CarbonateHCID 20322083N-(2,2-dipropoxyethyl)-N-(4-methyl-1,3-dioxan-2-ylmethyl)amine

Product 1

HCID 20322089N-(2,2-dipropoxyethyl)-N-(4-methyl-1,3-dioxan-2-ylmethyl)-alpha-chloroacetamide

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

N-(2,2-Dipropoxyethyl)-N-(4-methyl-1,3-dioxan-2-yl-methyl)amine (0.05 mole), benzene (100 ml), water (100 ml) and sodium carbonate (2 grams) are charged into a glass reaction vessel equipped with a mechanical stirrer and thermometer. The reaction mixture is cooled to a temperature of from 5° to 10° C and chloroacetyl chloride (0.05 mole) is added dropwise with stirring. After the addition is completed stirring is continued until the reaction mixture has reached 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-(2,2-dipropoxyethyl)-N-(4-methyl-1,3-dioxan-2-ylmethyl)-α-chloroacetamide as the residue.

Workup

  1. customequipped with a mechanical stirrer
  2. additionis added dropwise
  3. additionAfter the addition
  4. stirringis completed stirring
  5. customhas reached 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-e8e6d9bbffe74ddb8a5e6f4f52f38444
Source dataset
uspto-grants-1978_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04097491

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes