Acetic Acid → 4-methyl-7-Dimethylamino-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione

HRID 1844297노트

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HRID 1844297 반응식
[CH3:1][N:2]1[C:8](=[O:9])[C:7]2[CH:10]=[C:11](N)[CH:12]=[CH:13][C:6]=2[NH:5][C:4](=[O:15])[CH2:3]1.C=O.[BH3-][C:19]#[N:20].[Na+].[C:22](O)(=O)C>C(#N)C.C(OCC)C>[CH3:1][N:2]1[C:8](=[O:9])[C:7]2[CH:10]=[C:11]([N:20]([CH3:19])[CH3:22])[CH:12]=[CH:13][C:6]=2[NH:5][C:4](=[O:15])[CH2:3]1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 104429394-methyl-7-Amino-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione

생성물 1

HCID 704963004-methyl-7-Dimethylamino-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6342Acetonitrile용매

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온도
0 °C

실험 절차

To a solution of intermediate 3 (3.0 g, 13 mmol) and 37% aq formaldehyde (21 mL, 0.26 mol) in acetonitrile at 0° C., NaBH3CN (4.8 g, 77 mmol) was added portionwise. The reaction mixture was stirred at 0° C. for 2 h and then at room temperature for 1 h. Acetic acid (1.4 mL) was then added and the reaction mixture was stirred for another 2 h. The reaction mixture was poured into ethyl ether, washed with 2N KOH and the basic layer was extracted several times with ethyl acetate. The organic phases were collected and dried and solvents removed in vacuum to give an amorphous yellowish solid.

후처리

  1. waitat room temperature for 1 h
  2. stirringthe reaction mixture was stirred for another 2 h
  3. washwashed with 2N KOH
  4. extractionthe basic layer was extracted several times with ethyl acetate
  5. customThe organic phases were collected
  6. customdried
  7. customsolvents removed in vacuum
  8. customto give an amorphous yellowish solid

출처 및 근거

ORD 기록
ord-58f30c58fb134e38a5b4a8f842dca89c
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946410B2

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