Benzyl azide → 1-Phenylmethyl-4-(2,4,6-trimethylphenyl)-5-aminotriazole

HRID 277736

반응식

HRID 277736 반응식
[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH3:12])[C:3]=1[CH2:4][C:5]#[N:6].[CH2:13]([N:20]=[N+:21]=[N-:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CC(C)([O-])C.[K+]>O1CCCC1.O>[C:14]1([CH2:13][N:20]2[C:5]([NH2:6])=[C:4]([C:3]3[C:7]([CH3:12])=[CH:8][C:9]([CH3:11])=[CH:10][C:2]=3[CH3:1])[N:22]=[N:21]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

6

반응물 3

HCID 12152Benzyl azideHCID 5206982,4,6-TrimethylphenylacetonitrileHCID 23665647Potassium tert-butoxide

생성물 1

HCID 154869821-Phenylmethyl-4-(2,4,6-trimethylphenyl)-5-aminotriazole수율 61%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 2,4,6-trimethylbenzyl cyanide (1.0 g, 6.3 mmol), benzyl azide (0.92 g, 6.9 mmol) and potassium t-butoxide (0.78 g, 6.9 mmol) in tetrahydrofuran (10 mL) was stirred at ambient temperature for 2.5 days. The resulting suspension was diluted with water and extracted three times with ethyl acetate. The combined organic layers were dried over MgSO4 and filtered. Solvent was removed in vacuo to give a brown oil. Trituration with ether and filtration afforded a yellow solid (1.12 g, 61% yield): NMR (CDCl3, 300 MHz):7.60-7.30 (m, 5H), 7.30-7.20 (m, 2H), 5.50 (s, 2H), 3.18 (br s, 2H), 2.30 (s, 3H), 2.10 (s, 6H); CI-MS: 293 (M+H).

후처리

  1. extractionextracted three times with ethyl acetate
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. customSolvent was removed in vacuo
  5. customto give a brown oil
  6. filtrationTrituration with ether and filtration

출처 및 근거

ORD 기록
ord-ab652eea6daa4c4ea43e3f4aa3c4d422
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06358950B1

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