Formamide → 5H-s-triazolo[5,1-a]isoindole

HRID 436194노트

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HRID 436194 반응식
OS(O)(=O)=O.N[C:7]1[N:18]=[C:10]2[C:11]3[C:16]([CH2:17][N:9]2[N:8]=1)=[CH:15][CH:14]=[CH:13][CH:12]=3.N([O-])=O.[Na+].O[PH2]=O.C(N)=O.C(O)(=O)C.N1CCCCC1>O>[N:18]1[CH:7]=[N:8][N:9]2[CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]=12

참가 물질

8

반응물 6

HCID 713FormamideHCID 1118Sulfuric Acid2회HCID 4124402Phosphinic AcidHCID 9793820Piperidine, acetateHCID 214553042-Amino-5H-s-triazolo[5,1-a]isoindoleHCID 23668193Sodium Nitrite

생성물 1

HCID 132175355H-s-triazolo[5,1-a]isoindole수율 63%

시약·촉매·용매 1

HCID 962Water용매2회

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온도
1.5 °C

실험 절차

To a solution of 2 ml of 10% H2SO4 in 12 ml of water, a solution of 0.69 g (0.004 mole) of 2-amino -5H-s-triazolo[5,1-a]isoindole in 20 ml of water containing 4 ml of 10% H2SO4 is added. Under cooling to a 0-3°C, 8 ml of 0.5 N NaNO2 is dropped into the solution and 7.8 ml of 50% H3PO2 is successively added. After heating to about 40°C for 30 minutes, the mixture is filtered and the filtrate is brought to pH 8 with Na2CO3. The aqueous phase is extracted several times with ethyl ether and the organic extract is evaporated to dryness. The residual crude product is purified by crystallization from isopropyl ether. Yield 0.32 g (50%). M.p. 116- 7°C. The same compound may be obtained by heating at 140°C for 16 hours N-aminophthalimidine with an excess of formamide in the presence of a catalytic amount of piperidine acetate. Yield 63%.

후처리

  1. additionis successively added
  2. temperatureAfter heating to about 40°C for 30 minutes
  3. filtrationthe mixture is filtered
  4. extractionThe aqueous phase is extracted several times with ethyl ether
  5. extractionthe organic extract
  6. customis evaporated to dryness
  7. customThe residual crude product is purified by crystallization from isopropyl ether
  8. customThe same compound may be obtained

출처 및 근거

ORD 기록
ord-9f2c50a72c2b481a92cf1aaf80b635ee
출처 데이터셋
uspto-grants-1977_02
특허 번호
US04007276

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