1,3-Dichloroacetone → HCID 86753954, compound

HRID 1418935Notes

Reaction equation

HRID 1418935 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]2[CH:13]=[N:14][C:15]([C:16](=[S:18])[NH2:17])=[C:5]2[C@@H:4]2[CH2:19][CH2:20][N:3]12.[Cl:21][CH2:22][C:23](=O)[CH2:24]Cl>O1CCOCC1>[Cl:21][CH2:22][C:23]1[N:17]=[C:16]([C:15]2[N:14]=[CH:13][N:6]3[C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=4[C:2](=[O:1])[N:3]4[CH2:20][CH2:19][C@H:4]4[C:5]=23)[S:18][CH:24]=1

Participants

4

Reactant 2

HCID 107931,3-DichloroacetoneHCID 86753953HCID 86753953, compound

Product 1

HCID 86753954HCID 86753954, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A yellow suspension of 4.86 g (0.0171 mol) of (S)-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[l,5-a][1,4]benzodiazepine-1-thiocarboxamide in 120 ml of dioxan was treated with 2.38 g (0.0188 mol) of 1,3-dichloro-2-propanone. The suspension was boiled at reflux for 48 hrs. The solution obtained was cooled and completely freed from the solvents. The product was chromatographed over silica gel with dichloromethane/ethyl acetate 1:1 as the eluent and recrystallized from hot ethyl acetate. There were obtained 2.54 g (42%) of (S)-1-(4-chloromethyl-thiazol-2-yl)-12,12a-dihydro-9H,11H-azeto[2,1-c]-imidazo[1,5-a][1,4]benzodiazepin-9-one as white crystals; m.p. 248°-249° and [α]D20 =-186.1° (DMF, c=1%).

Workup

  1. temperatureat reflux for 48 hrs
  2. customThe solution obtained
  3. temperaturewas cooled
  4. customThe product was chromatographed over silica gel with dichloromethane/ethyl acetate 1:1 as the eluent
  5. customrecrystallized from hot ethyl acetate

Sources & evidence

ORD record
ord-56e0e06673f14470934c20182d1e3df4
Source dataset
uspto-grants-1999_03
Patent number
US05885986

Reaction notes

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