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Triethylamine → 2-(Diaminomethyleneamino)-4-[2-(2-cyano-3-methylguanidino)methylthiazol-4-yl]thiazole

HRID 1491865
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HRID 1491865 반응식
Cl.Cl.[NH2:3][CH2:4][C:5]1[S:6][CH:7]=[C:8]([C:10]2[N:11]=[C:12]([N:15]=[C:16]([NH2:18])[NH2:17])[S:13][CH:14]=2)[N:9]=1.[C:19]([N:21]=[C:22](SC)SC)#[N:20].[CH2:27]([N:29](CC)CC)C>CN(C)C=O>[NH2:17][C:16](=[N:15][C:12]1[S:13][CH:14]=[C:10]([C:8]2[N:9]=[C:5]([CH2:4][NH:3][C:19]([NH:21][CH3:22])=[N:20][C:27]#[N:29])[S:6][CH:7]=2)[N:11]=1)[NH2:18]
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 189538344-(2-Aminomethylthiazol-4-yl)-2-(diaminomethyleneamino)thiazole dihydrochloride

생성물 1

HCID 1784850392-(Diaminomethyleneamino)-4-[2-(2-cyano-3-methylguanidino)methylthiazol-4-yl]thiazole수율 19.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide
용매

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온도
70 °C

실험 절차

A suspension of 4-(2-aminomethylthiazol-4-yl)-2-(diaminomethyleneamino)thiazole dihydrochloride (1.0 g), dimethyl N-cyanodithiocarbonimidate (0.45 g) and triethyl amine (0.7 g) in N,N-dimethylformamide (40 ml) was heated at 70° C. for 10 hours. 40% methylamino solution (5 ml) was added to the reaction mixture and the mixture was stirred at room temperature for 14 hours. The solvent was removed under reduced pressure. The residue was suspended in water (30 ml) and the mixture was alkalized to pH 10 with a saturated aqueous potassium carbonate solution. The resulting precipitate was collected by filtration. Recrystallization from a mixture of N,N-dimethylformamide and water afforded 2-(diaminomethyleneamino)-4-[2-(2-cyano-3-methylguanidino)methylthiazol-4-yl]thiazole (0.2 g).

후처리

  1. addition40% methylamino solution (5 ml) was added to the reaction mixture
  2. customThe solvent was removed under reduced pressure
  3. filtrationThe resulting precipitate was collected by filtration
  4. customRecrystallization
  5. additionfrom a mixture of N,N-dimethylformamide and water

출처 및 근거

ORD 기록
ord-db651b0f355e48bb90920c970de37a32
출처 데이터셋
uspto-grants-1994_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05371097

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