p-Toluenesulfonic acid → Desmethylnitrazolam

HRID 1764535노트

반응식

HRID 1764535 반응식
[NH:1]([C:3]1[CH2:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6]2[CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=[CH:19][C:5]=2[N:4]=1)[NH2:2].N[C:24]1CN=C(C2C=CC=CC=2)C2C=C([N+]([O-])=O)C=CC=2N=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C([O-])([O-])OCC.C(Cl)(Cl)Cl>[N+:20]([C:17]1[CH:18]=[CH:19][C:5]2[N:4]3[CH:24]=[N:2][N:1]=[C:3]3[CH2:9][N:8]=[C:7]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:6]=2[CH:16]=1)([O-:22])=[O:21]

참가 물질

6

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 21265982HCID 21265982, 화합물HCID 22768399HCID 22768399, 화합물

생성물 1

HCID 20317280Desmethylnitrazolam

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 53630039Ethylorthoformate용매

실험 절차

2-Hydrazino-7-nitro-5-phenyl-3H-1,4-benzodiazepine prepared from 5.6 parts of 2-amino-7-nitro-5-phenyl-3H-1,4-benzodiazepine in a similar manner to Example 7, is dissolved in a mixture of 20 parts by volume of ethyl orthoformate and 100 parts by volume of chloroform, followed by the addition of 10 parts of p-toluenesulfonic acid. The whole mixture is left standing at room temperature for 1 hour with occasional shaking. After completion of the reaction, the solution is washed with a saturated aqueous solution of sodium bicarbonate, then with water, and dried over sodium sulfate. After evaporation of the solvent, the residue is treated with ethyl acetate, whereby 8-nitro-6-phenyl-4H-s-triazolo [4,3-a][1,4] benzodiazepine is yielded as crystals. Recrystallization from tetrahydrofuran yields pale yellow needles melting at 271° C to 272° C.

후처리

  1. waitThe whole mixture is left
  2. customAfter completion of the reaction
  3. washthe solution is washed with a saturated aqueous solution of sodium bicarbonate
  4. dry with materialwith water, and dried over sodium sulfate
  5. customAfter evaporation of the solvent
  6. additionthe residue is treated with ethyl acetate

출처 및 근거

ORD 기록
ord-533073bec3c2449e8f00ad737e7484a5
출처 데이터셋
uspto-grants-1978_09
특허 번호
US04116956

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