Dimethylformamide → HCID 178505372, 화합물

HRID 375818

반응식

HRID 375818 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.ClC[S:18][C:19]#N.C[N:22]([CH3:25])C=O>O>[C:4]1([C:10]2[C:11]([S:1][C:25]#[N:22])=[N:12][SH:13]([S:18][CH3:19])[N:14]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 14804Sodium SulfideHCID 76755Thiocyanic acid, chloromethyl esterHCID 27640443-Chloro-4-phenyl-1,2,5-thiadiazole

생성물 1

HCID 178505372HCID 178505372, 화합물수율 69%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a stirred solution of 3.81 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 18 hours and to this mixture was added 6.68 g (1.5 molar equivalents) of chloromethyithiocyanate. This mixture was stirred for ~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 8.99 g (83 percent of theoretical) as an oil. Upon crystallization, a light yellow solid melting at 58°-60° C. was recovered in a yield of 69 percent of theoretical; 1H NMR (300 MHz, CDCl3)δ 4.77 (s, 2H), 7.49 (m, 3H), 7.82 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 38.28, 111.46, 127.97, 128.78, 130.06, 151.77, 157.93; MS (EI) m/e 265(M+), 207, 148, 116.

후처리

  1. stirringThis mixture was stirred for ~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 8.99 g (83 percent of theoretical) as an oil
  10. customUpon crystallization
  11. customa light yellow solid melting at 58°-60° C. was recovered in a yield of 69 percent of theoretical

출처 및 근거

ORD 기록
ord-49454a63985149eb8a4310d832360a89
출처 데이터셋
uspto-grants-1996_01
특허 번호
US05488060

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