Dichloroacetyl chloride → HCID 12923515, compound

HRID 544187Notes

Reaction equation

HRID 544187 reaction equation
C(N(CC)CC)C.[CH3:8][C:9]12[CH2:17][CH2:16][C:15](=[O:18])[N:14]1[CH2:13][CH2:12][CH2:11][NH:10]2.[Cl:19][CH:20]([Cl:24])[C:21](Cl)=[O:22]>C1(C)C=CC=CC=1>[Cl:19][CH:20]([Cl:24])[C:21]([N:10]1[C:9]2([CH3:8])[N:14]([C:15](=[O:18])[CH2:16][CH2:17]2)[CH2:13][CH2:12][CH2:11]1)=[O:22]

Participants

5

Reactant 3

HCID 6593Dichloroacetyl chlorideHCID 8471TriethylamineHCID 3161164Hexahydro-8a-methylpyrrolo[1,2-a]pyrimidin-6(2H)-one

Product 1

HCID 12923515HCID 12923515, compoundYield 66.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-10 °C

Procedure

10.5 g (0.105 mole) of triethylamine are added to a solution of 15.4 g (0.1 mole) of 6-methyl-9-oxo-1,5-diazabicyclo[4.3.0]nonane in 100 ml of toluene. The mixture is cooled to -10° C. and 14.8 g (0.1 mole) of dichloroacetyl chloride are added dropwise at from -10° to -5° C. The batch is stirred for a further 4 hours and the triethylamine hydrochloride which has precipitated is filtered off. After evaporating the toluene from the filtrate, crystals separate out, and these can be recrystallized from a 1:3 toluene/acetone mixture. 17.7 g of 5-dichloroacetyl-6-methyl-9-oxo-1,5-diazabicyclo[4.3.0]nonane, a melting point 144°-147° C., are obtained.

Workup

  1. customthe triethylamine hydrochloride which has precipitated
  2. filtrationis filtered off
  3. customAfter evaporating the toluene from the filtrate, crystals
  4. customseparate out
  5. customthese can be recrystallized from a 1:3 toluene/acetone mixture

Sources & evidence

ORD record
ord-c6a8a21c8676430ca8e8cd53b98dbeb4
Source dataset
uspto-grants-1984_05
Patent number
US04448960

Reaction notes

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