Malononitrile → HCID 9926256, 화합물

HRID 1814731

반응식

HRID 1814731 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]([CH3:14])[S:12][C:11](=[O:15])[NH:10][N:9]=2)=[CH:4][CH:3]=1.[N:16]([O-])=O.[Na+].[C:20](#[N:24])[CH2:21][C:22]#[N:23].C([O-])(=O)C.[Na+]>O.Cl.C(O)(C)(C)C>[CH3:14][CH:13]1[S:12][C:11](=[O:15])[NH:10][N:9]=[C:8]1[C:5]1[CH:4]=[CH:3][C:2]([NH:1][N:16]=[C:21]([C:20]#[N:24])[C:22]#[N:23])=[CH:7][CH:6]=1

참가 물질

8

반응물 4

HCID 8010MalononitrileHCID 517045Sodium AcetateHCID 224986135-(4-aminophenyl)-6-methyl-3H,6H-1,3,4-thiadiazine-2-oneHCID 23668193Sodium Nitrite

생성물 1

HCID 9926256HCID 9926256, 화합물수율 95%

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 962Water용매3회HCID 6386tert-Butanol용매

반응 조건

온도
0 °C

실험 절차

(+) 5-(4-aminophenyl)-6-methyl-3,6-dihydro-[1,3,4]-thiadiazin-2-one (1.34 g, 6 mmol) was dissolved in water (23 ml) and 6 N hydrochloric acid (4.5 ml). The solution was stirred and cooled. A cooled solution of sodiumnitrite (0.5 g) in water (5 ml) was added. Then a cooled solution of malononitrile (0.9 g) in t-butanol (54 ml) was added. In the end to the solution was added a cooled solution of sodium acetate (5.4 g) diluted in water (40 ml). The reaction mixture was stirred under cooling (0° C.) for 3 hours. After stirring the crystalline product was filtered and washed with water, yielding (+)-[[4-(3,6-dihydro-6-methyl-2-oxo-2H-1,3,4-thiadiazin-5-yl)phenyl]hydrazono]propanedinitrile as a crystalline solid (1.7 g) with optical purity of 100%, chromatografic purity 99.3%, m.p. 125-128° C., [a]D25=+1002°.

후처리

  1. temperaturecooled
  2. stirringThe reaction mixture was stirred
  3. stirringAfter stirring the crystalline product
  4. filtrationwas filtered
  5. washwashed with water

출처 및 근거

ORD 기록
ord-4c2ee9a6df964315988578e4e8473200
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06878702B2

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