Cyanoacetic acid hydrazide → HCID 12562505, 화합물

HRID 597070

반응식

HRID 597070 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=S)[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=2[CH:19]=1.[C:20]([CH2:22][C:23]([NH:25][NH2:26])=O)#[N:21]>C(O)CCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:23]([CH2:22][C:20]#[N:21])=[N:25][N:26]=[C:10]3[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=2[CH:19]=1

참가 물질

4

반응물 2

HCID 8820Cyanoacetic acid hydrazideHCID 826706Thionordiazepam

생성물 1

HCID 12562505HCID 12562505, 화합물

시약·촉매·용매 1

HCID 2631-Butanol용매

실험 절차

A mixture of 1,3-dihydro-7-chloro-5-phenyl-2H-1,4-benzodiazepine-2-thione (5.72 g., 0.02 mole), cyanoacetic acid hydrazide (5.95 g., 0.06 mole) and n-butylalcohol (275 ml.) is refluxed for 7.5 hours with a slow stream of nitrogen bubbling through the mixture. The mixture is then concentrated in vacuo. The resulting residue is suspended in water and extracted with methylene chloride. The extract was dried and concentrated. The residue is chromatographed on silica gel (400 g.) with 2% methanol- 98% CHCl3. The product eluted from the column is crystallized from ethyl acetate-Skellysolve B hexanes to give 2.62 g. of 8-chloro-6-phenyl-4H-s-triazolo[4,3a][1,4]benzodiazepine-1-acetonitrile of melting point 198°-201° C.

후처리

  1. temperatureis refluxed for 7.5 hours with a slow stream of nitrogen bubbling through the mixture
  2. concentrationThe mixture is then concentrated in vacuo
  3. extractionextracted with methylene chloride
  4. customThe extract was dried
  5. concentrationconcentrated
  6. customThe residue is chromatographed on silica gel (400 g.) with 2% methanol- 98% CHCl3
  7. washThe product eluted from the column
  8. customis crystallized from ethyl acetate-Skellysolve B hexanes
  9. customto give 2.62 g

출처 및 근거

ORD 기록
ord-fdd650ad424349b2a7679bb70ae0f147
출처 데이터셋
uspto-grants-1977_03
특허 번호
US04012413

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