2-Propanol, reaction products with ammonia, distn. residues → 2H-1,4-Benzodiazepin-2-one

HRID 860807ノート

反応式

HRID 860807 の反応式
N.CC(O)C.ClC(C1C=CC(Cl)=CC=1)(C1N(C)C=NC=1)[C:8]1[CH:9]=[CH:10][C:11]2[N:17](C)[C:16](=[O:19])[CH2:15][N:14]=[C:13](C3C=CC=C(Cl)C=3)[C:12]=2[CH:27]=1>C1COCC1>[N:17]1[C:16](=[O:19])[CH:15]=[N:14][CH:13]=[C:12]2[CH:27]=[CH:8][CH:9]=[CH:10][C:11]=12

参加物

4

反応物 2

HCID 183319422-Propanol, reaction products with ammonia, distn. residuesHCID 69020457HCID 69020457、化合物

生成物 1

HCID 218646392H-1,4-Benzodiazepin-2-one収率 151.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
5 °C

実験手順

NH3/2-propanol (40 ml) was added dropwise at 5° C. to a mixture of 7-[chloro(4-chlorophenyl)(1-methyl-1H-imidazol-5-yl)methyl]-5-(3-chlorophenyl)-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one (described in Example B10a) (0.0075 mol) in THF (40 ml). The mixture was stirred at 5° C. for 30 min, hydrolyzed and extracted with DCM. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated till dryness. The residue (4 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 97.5/2.5/0.1 and 96/4/0.1; 15–40 μm). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from acetonitrile and diethyl ether. The precipitate was filtered off and dried, yielding 1.8 g (48%) of 2H-1,4-benzodiazepin-2-one, 7-[amino(4-chlorophenyl)(1-methyl-1H-imidazol-5-yl)methyl]-5-(3-chlorophenyl)-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one, mp. 213° C.

後処理

  1. extractionhydrolyzed and extracted with DCM
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated till dryness
  6. customThe residue (4 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 97.5/2.5/0.1 and 96/4/0.1; 15–40 μm)
  7. customThe pure fractions were collected
  8. customthe solvent was evaporated
  9. customThe residue was crystallized from acetonitrile and diethyl ether
  10. filtrationThe precipitate was filtered off
  11. customdried

出典と根拠

ORDレコード
ord-bc24aaf550774d978b2902aca1f54434
出典データセット
uspto-grants-2006_12
特許番号
US07153958B2

反応ノート

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