Cyanogen Bromide → 4-Phenyl-3-thiocyanato-1,2,5-thiadiazole

HRID 375817

반응식

HRID 375817 반응식
[S-2:1].[Na+].[Na+].[C:4]1([C:10]2[C:11](Cl)=[N:12][S:13][N:14]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[N:16]#[C:17]Br>CN(C)C=O.O>[C:4]1([C:10]2[C:11]([S:1][C:17]#[N:16])=[N:12][S:13][N:14]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

참가 물질

6

반응물 3

HCID 10476Cyanogen BromideHCID 14804Sodium SulfideHCID 27640443-Chloro-4-phenyl-1,2,5-thiadiazole

생성물 1

HCID 153374974-Phenyl-3-thiocyanato-1,2,5-thiadiazole

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of 3.8 grams(g)(0.05 mole) of sodium sulfide in 100 mL of dimethylformamide was added 8 g(0.041 mole) of 4-Phenyl-3-chloro-1,2,5-thiadiazole. The mixture was stirred overnight (~16 hours), and to the resulting dark green solution was added 6.64 g(1.5 molar equivalents) of cyanogen bromide. This mixture was stirred for about 14 hours and then diluted with 100 mL of water and extracted with 200 mL of methylene chloride. The organic layer was separated and washed with water (2×100 mL), dried and concentrated under reduced pressure. The thus recovered crude material was chromatographed on silica gel with a 10% EtoAc:90% hexane mixture to yield 6.6 g (72 percent of theoretical) as an oil which turned to a white solid melting at 49° C. upon standing; 13C NMR (75 MHz, CDCl3) δ 159.10, 141.78, 130.59, 129.76, 129.06, 127.88, 105.98; MS (EI) m/e 219(M+), 192, 160, 135, 103.

후처리

  1. stirringThis mixture was stirred for about 14 hours
  2. extractionextracted with 200 mL of methylene chloride
  3. customThe organic layer was separated
  4. washwashed with water (2×100 mL)
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe thus recovered crude material
  8. customwas chromatographed on silica gel with a 10% EtoAc
  9. custom90% hexane mixture to yield 6.6 g (72 percent of theoretical) as an oil which

출처 및 근거

ORD 기록
ord-b1f292df84a140e38b591869d9253f42
출처 데이터셋
uspto-grants-1996_01
특허 번호
US05488060

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