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Chloroacetyl chloride → N-alpha-chloroacetyl-N-(1,3-dioxepan-2-ylmethyl)-2,6-diethylaniline

HRID 267465
Notes
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Reaction equation

HRID 267465 reaction equation
[O:1]1[CH2:7][CH2:6][CH2:5][CH2:4][O:3][CH:2]1[CH2:8][NH:9][C:10]1[C:15]([CH2:16][CH3:17])=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:18][CH3:19].C(=O)(O)[O-].[Na+].O1CCOCC1.[Cl:31][CH2:32][C:33](Cl)=[O:34]>CCOCC.O>[Cl:31][CH2:32][C:33]([N:9]([CH2:8][CH:2]1[O:3][CH2:4][CH2:5][CH2:6][CH2:7][O:1]1)[C:10]1[C:15]([CH2:16][CH3:17])=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:18][CH3:19])=[O:34]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 21548999N-(1,3-dioxepan-2-ylmethyl)-2,6-diethylaniline

Product 1

HCID 21403978N-alpha-chloroacetyl-N-(1,3-dioxepan-2-ylmethyl)-2,6-diethylaniline

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 3283Diethyl EtherSolvent

Procedure

N-(1,3-dioxepan-2-ylmethyl)-2,6-diethylaniline (26.3 grams), sodium bicarbonate (15 grams), dioxane (30 ml) and water (4 ml) are charged into a glass reaction vessel equipped with a mechanical stirrer and thermometer. The mixture is cooled to a temperature of about 0°C and chloroacetyl chloride (15 grams) is added, with stirring, over a period of about 15 minutes. After the addition is completed stirring is continued for a period of about 1 hour. After this time ether (100 ml) is added to the mixture and the resulting solution is washed with water. The washed solution is then dried over anhydrous magnesium sulfate and stripped of solvents leaving a solid residue. The residue is recrystallized to yield the desired product N-α-chloroacetyl-N-(1,3-dioxepan-2-ylmethyl)-2,6-diethylaniline.

Workup

  1. customequipped with a mechanical stirrer
  2. additionis added
  3. additionAfter the addition
  4. stirringis completed stirring
  5. waitis continued for a period of about 1 hour
  6. washthe resulting solution is washed with water
  7. dry with materialThe washed solution is then dried over anhydrous magnesium sulfate
  8. customleaving a solid residue
  9. customThe residue is recrystallized

Sources & evidence

ORD record
ord-6a716169c2294e41bcee1fc53e523afe
Source dataset
uspto-grants-1976_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US03942972

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes