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

HRID 436194ノート

反応式

HRID 436194 の反応式
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

参加物

8

反応物 6

HCID 713FormamideHCID 1118Sulfuric Acid2 回HCID 4124402Phosphinic AcidHCID 9793820Piperidine, acetateHCID 214553042-Amino-5H-s-triazolo[5,1-a]isoindoleHCID 23668193Sodium Nitrite

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

反応条件

温度
1.5 °C

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-9f2c50a72c2b481a92cf1aaf80b635ee
出典データセット
uspto-grants-1977_02
特許番号
US04007276

反応ノート

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