Hydrochloric Acid → (3-Benzyloxy-4-nitrophenyl)acetonitrile

HRID 1358457

반응식

HRID 1358457 반응식
[OH-].[Na+].C([C:10]1[C:11]([N+:33]([O-:35])=[O:34])=[C:12]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][C:24]3C=CC=CC=3)C=2[N+]([O-])=O)[CH:13]=[CH:14][CH:15]=1)C1C=CC=CC=1.C1(S[CH2:43][C:44]#[N:45])C=CC=CC=1.Cl>CS(C)=O>[CH2:17]([O:16][C:12]1[CH:13]=[C:14]([CH2:43][C:44]#[N:45])[CH:15]=[CH:10][C:11]=1[N+:33]([O-:35])=[O:34])[C:22]1[CH:21]=[CH:20][CH:19]=[CH:23][CH:24]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 78891(Phenylthio)acetonitrileHCID 57359178Benzyl-2-nitrophenyl Ether

생성물 1

HCID 13629306(3-Benzyloxy-4-nitrophenyl)acetonitrile

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매2회

실험 절차

To a suspension of NaOH (68.44 g 1.71 mol, Aldrich, 20-40 mesh beads) in 171 mL of DMSO a solution of benzyl-2-nitrophenyl ether (39.23 g, 0.171 mol) and (phenylthio)acetonitrile (25.54 g, 0.171 mol, Lancaster) in 171 mL of DMSO was added dropwise for 10 min and stirred at r.t. for another 25 min. A mixture of 430 g of ice and 430 g of conc. HCl was added. The product precipitated and crystallized. The reaction mixture was cooled down in a refrigerator and filtered. The precipitate was dried on air (hood!) and recrystallized from EtOAc-hexanes. Yield 32.03 g (70%), mp 78-80° C.

후처리

  1. additionwas added dropwise for 10 min
  2. additionwas added
  3. customThe product precipitated
  4. customcrystallized
  5. temperatureThe reaction mixture was cooled down in a refrigerator
  6. filtrationfiltered
  7. customThe precipitate was dried on air (hood!)
  8. customrecrystallized from EtOAc-hexanes

출처 및 근거

ORD 기록
ord-07042c1f284e4e9f9227e21fb80c0ce4
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06596734B1

연결된 노트

불러오는 중…