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

HRID 860807노트

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HRID 860807 반응식
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

참가 물질

4

반응물 2

HCID 183319422-Propanol, reaction products with ammonia, distn. residuesHCID 69020457HCID 69020457, 화합물

생성물 1

HCID 218646392H-1,4-Benzodiazepin-2-one수율 151.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
5 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bc24aaf550774d978b2902aca1f54434
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07153958B2

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