Water → HCID 21866225, 화합물

HRID 857786노트

반응식

HRID 857786 반응식
[N:1]([CH2:4][C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[C:12]1[C:16]([Cl:17])=[N:15][S:14][N:13]=1)=[N+]=[N-].O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH-].[K+]>C1COCC1.CO>[Cl:11][C:9]1[CH:8]=[CH:7][C:6]([C:12]2[C:16]([Cl:17])=[N:15][S:14][N:13]=2)=[C:5]([CH2:4][NH2:1])[CH:10]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 14797Potassium HydroxideHCID 21866197HCID 21866197, 화합물

생성물 1

HCID 21866225HCID 21866225, 화합물

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of 3-[2-(azidomethyl)-4-chlorophenyl]-4-chloro-1,2,5-thiadiazole (0.205 g, 0.72 mmol) and water (0.01 mL, 0.72 mmol) in THF (1.5 mL) was added triphenyl phosphine (0.188 g, 0.72 mmol). The solution was refluxed 1 h then stirred at ambient temperature for 16 h. The solution was reduced in vacuo and the residue was dissolved in MeOH. KOH (1 pellet) was added and the solution was refluxed 5 min. The solution was reduced in vacuo and partitioned between 1 M HCl and EtOAc. The aqueous phase was separated, basified with 1 M NaOH and extracted into ether. The organic phase was separated, dried (Na2SO4) and reduced in vacuo. The residue was purified by flash chromatography on silica (eluting with EtOAc/hexanes gradient, 5–10% EtOAc followed by 0.9% MeOH/0.1% NH4OH/chloroform). 1-[5-Chloro-2-(4-chloro-1,2,5-thiadiazole-3-yl)phenyl]methanamine was isolated as a yellow oil. MS m/z=260.5.

후처리

  1. temperatureThe solution was refluxed 1 h
  2. temperaturethe solution was refluxed 5 min
  3. custompartitioned between 1 M HCl and EtOAc
  4. customThe aqueous phase was separated
  5. extractionextracted into ether
  6. customThe organic phase was separated
  7. dry with materialdried (Na2SO4)
  8. customThe residue was purified by flash chromatography on silica (eluting with EtOAc/hexanes gradient, 5–10% EtOAc followed by 0.9% MeOH/0.1% NH4OH/chloroform)

출처 및 근거

ORD 기록
ord-563f947af26b42969b779b7000f47b33
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07144899B2

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