Sulfuric Acid → HCID 21562299, compound
Reaction equation
S(=O)(=O)(O)O.[Cl:6][C:7]1[CH:8]=[CH:9][C:10]2[N:16]=[C:15]([NH:17][CH2:18][C:19]#[C:20][CH3:21])[CH2:14][N:13]=[C:12]([C:22]3[C:27]([F:28])=[CH:26][CH:25]=[CH:24][C:23]=3[F:29])[C:11]=2[CH:30]=1.[OH-].[Na+]>>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]2[N:16]3[C:19]([CH2:20][CH3:21])=[CH:18][N:17]=[C:15]3[CH2:14][N:13]=[C:12]([C:22]3[C:23]([F:29])=[CH:24][CH:25]=[CH:26][C:27]=3[F:28])[C:11]=2[CH:30]=1Participants
Procedure
To 10 ml. of ice cold 50% (wt) sulfuric acid is added successively with stirring under nitrogen 0.01 mole of 7-chloro-5-(2,6-difluorophenyl)-2-(2-butynylamino)-3H-1,4-benzodiazepine (IV) and 0.132 g. of mercuric sulfate. The resulting mixture is stirred for about 18 hours, poured into ice water, neutralized with 15% aqueous sodium hydroxide solution and extracted with chloroform. The extract thus obtained is dried over potassium carbonate and concentrated in vacuo. The residue thus obtained is chromatographed on silica gel with chloroform containing 1% methanol. The eluates containing the desired product are combined, concentrated in vacuo and crystallized from ethyl acetate-hexanes to give 8-chloro-6-(2,6-difluorophenyl)-1-ethyl-4H-imidazo[1,2-a][1,4]benzodiazepine.
Workup
- extractionextracted with chloroform
- extractionThe extract thus
- customobtained
- dry with materialis dried over potassium carbonate
- concentrationconcentrated in vacuo
- customThe residue thus obtained
- customis chromatographed on silica gel with chloroform containing 1% methanol
- additionThe eluates containing the desired product
- concentrationconcentrated in vacuo
- customcrystallized from ethyl acetate-hexanes
Sources & evidence
- ORD record
- ord-3c518890d5ef4aca8bdd0596d0f56570
- Source dataset
- uspto-grants-1976_01
- Patent number
- US03933794
Reaction notes
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