Hydrazine hydrate (1:1) → 4-[alpha-Amino-4-chloro-alpha-(o-chlorophenyl)-o-tolyl]-3-[(dimethylamino)methyl]-5-methyl-4h-1,2,4-triazole

HRID 918263

반응식

HRID 918263 반응식
ClC1C=CC2N3C(C4CC4)=NN=C3[CH2:9][N:8]=[C:7](C3C=CC=CC=3Cl)C=2C=1.O.NN.[NH2:29][CH:30]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=1[Cl:53])[C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]=1[N:38]1[C:42]([CH3:43])=[N:41][N:40]=[C:39]1[CH:44]1CC1>C(O)COCCO>[NH2:29][CH:30]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=1[Cl:53])[C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]=1[N:38]1[C:42]([CH3:43])=[N:41][N:40]=[C:39]1[CH2:44][N:8]([CH3:9])[CH3:7]

참가 물질

5

반응물 3

HCID 24654Hydrazine hydrate (1:1)HCID 867337158-chloro-6-(o-chlorophenyl)-1-cyclopropyl-4H-s-triazolo[4,3-a][1,4] benzodiazepineHCID 867337164-[alpha-amino-4-chloro-alpha(o-chlorophenyl)-o-tolyl]-3-cyclopropyl-5-methyl-4H-1,2,4-triazole

생성물 1

HCID 867337144-[alpha-Amino-4-chloro-alpha-(o-chlorophenyl)-o-tolyl]-3-[(dimethylamino)methyl]-5-methyl-4h-1,2,4-triazole

시약·촉매·용매 1

HCID 8117Diethylene Glycol용매

실험 절차

A solution of 7.38 g. of 8-chloro-6-(o-chlorophenyl)-1-(dimethylamino)methyl-4H-s-triazolo[4,3 -a][1,4] benzodiazepine (III) (20.0 mmol.) and 5.0 ml. of hydrazine hydrate in 50 ml. of diethylene glycol is heated to about 140° C. for about 18 hours. The reaction is quenched in a cold aqueous 5% sodium hydroxide solution, and the product extracted with chloroform. The extracts are dried and concentrated in vacuo to yield 8.5 g. of oil, which is crystallized from ethyl acetate/hexane mixtures to give 4.0 g. of 4-[α-amino-4-chloro-α-(o-chlorophenyl)-o-tolyl]-3-[(dimethylamino)methyl]-5-methyl-4H-1,2,4 -triazole (I), isomer A, m.p. 142°-144° C., an analytical sample of which melts at 148°-150° C. and has infrared (mull) spectral absorptions at 3380, 3270, 3200, 3070, 2770, 1610, 1590, 1570, 1530 and 1520 cm-1.

후처리

  1. customThe reaction is quenched in a cold aqueous 5% sodium hydroxide solution
  2. extractionthe product extracted with chloroform
  3. customThe extracts are dried
  4. concentrationconcentrated in vacuo
  5. customto yield 8.5 g
  6. customof oil, which is crystallized from ethyl acetate/hexane
  7. customto give 4.0 g

출처 및 근거

ORD 기록
ord-dce2467bfab9484b836a4426c9b1c792
출처 데이터셋
uspto-grants-1976_07
특허 번호
US03970666

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