Sodium Azide → 4-azido-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran

HRID 1492457노트

반응식

HRID 1492457 반응식
Br[CH:2]1[C:7]2[CH:8]=[C:9]([C:12]#[N:13])[CH:10]=[CH:11][C:6]=2[O:5][C:4]([CH3:15])([CH3:14])[CH2:3]1.[N-:16]=[N+:17]=[N-:18].[Na+]>CN(C)C=O>[N:16]([CH:2]1[C:7]2[CH:8]=[C:9]([C:12]#[N:13])[CH:10]=[CH:11][C:6]=2[O:5][C:4]([CH3:15])([CH3:14])[CH2:3]1)=[N+:17]=[N-:18]

참가 물질

4

반응물 2

HCID 33557Sodium AzideHCID 102446284-bromo-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran

생성물 1

HCID 101051694-azido-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran수율 97.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 4-bromo-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran (6.73 g, 25.29 mmoles), title B compound, in dry N,N-dimethylformamide (100 mL) was treated with sodium azide (3.79 g, 50.57 mmoles) and stirred at room temperature under argon for four hours. The reaction mixture was partitioned between 100 mL ethyl acetate and 200 mL distilled water. The organic layer was separated and the aqueous layer was extracted with 100 mL of ethyl acetate. The combined organics were washed successively with distilled water, saturated sodium bicarbonate solution, brine and dried over magnesium sulfate. The solvent was evaporated under vacuum to obtain an orange gum (5.62 g) which was triturated with penme to provide the title compound (4.50 g, 78%) as an off-white solid, m.p. 63°-64° C.

후처리

  1. customThe reaction mixture was partitioned between 100 mL ethyl acetate and 200 mL
  2. distillationdistilled water
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with 100 mL of ethyl acetate
  5. washThe combined organics were washed successively with distilled water, saturated sodium bicarbonate solution, brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated under vacuum

출처 및 근거

ORD 기록
ord-e500ae6e52f74346a7b7670cf9949c7f
출처 데이터셋
uspto-grants-1994_12
특허 번호
US05374643

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