1,3-Dichloroacetone → HCID 21842289, compound

HRID 1737345Notes

Reaction equation

HRID 1737345 reaction equation
[CH3:1][N:2]1[C:8](=[O:9])[C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[N:5]2[CH:14]=[N:15][C:16]([C:17](=[S:19])[NH2:18])=[C:4]2[CH2:3]1.[Cl:20][CH2:21][C:22](=O)[CH2:23]Cl>O1CCOCC1>[Cl:20][CH2:21][C:22]1[N:18]=[C:17]([C:16]2[N:15]=[CH:14][N:5]3[C:6]4[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=4[C:8](=[O:9])[N:2]([CH3:1])[CH2:3][C:4]=23)[S:19][CH:23]=1

Participants

4

Reactant 2

HCID 107931,3-DichloroacetoneHCID 21842269HCID 21842269, compound

Product 1

HCID 21842289HCID 21842289, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A yellow suspension of 8.60 g (0.0316 mol) of 5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-thiocarboxamide in 200 ml of dioxan was treated with 4.41 g (0.0347 mol) of 1,3-dichloro-2-propanone. The suspension was boiled at reflux for 3 hrs., cooled and filtered. The solution was boiled at reflux for a further 16 hrs., cooled and suction filtered. The product was recrystallized from hot acetonitrile. There were obtained 5.4 g (65%) of 3-(4-chloromethyl-thiazol-2-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one as white crystals. An analytical sample could be obtained from the mother liquor after chromatography (silica gel, cyclohexane/ethyl acetate 1:1) and recrystallization (acetonitrile); m.p. 248-249°.

Workup

  1. temperatureat reflux for 3 hrs
  2. temperature, cooled
  3. filtrationfiltered
  4. temperatureat reflux for a further 16 hrs
  5. temperature, cooled
  6. filtrationsuction filtered
  7. customThe product was recrystallized from hot acetonitrile

Sources & evidence

ORD record
ord-ceb074ece21e4ddca01b15ab65432f9a
Source dataset
uspto-grants-1999_10
Patent number
US05962450

Reaction notes

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