Tributyltin azide → N-Ethyl-N'-[6-(2H-1,2,3,4-tetraazol-5-yl)-1,3-benzothiazol-2-yl]urea

HRID 9175

반응식

HRID 9175 반응식
[C:1]([C:3]1[CH:17]=[CH:16][C:6]2[N:7]=[C:8]([NH:10][C:11]([NH:13][CH2:14][CH3:15])=[O:12])[S:9][C:5]=2[CH:4]=1)#[N:2].[N:18]([Sn](CCCC)(CCCC)CCCC)=[N+:19]=[N-:20]>O1CCCC1>[CH2:14]([NH:13][C:11]([NH:10][C:8]1[S:9][C:5]2[CH:4]=[C:3]([C:1]3[N:18]=[N:19][NH:20][N:2]=3)[CH:17]=[CH:16][C:6]=2[N:7]=1)=[O:12])[CH3:15]

참가 물질

4

반응물 2

HCID 4984872Tributyltin azideHCID 21985533N-(6-Cyano-1,3-benzothiazol-2-yl)-N'-ethylurea

생성물 1

HCID 21985643N-Ethyl-N'-[6-(2H-1,2,3,4-tetraazol-5-yl)-1,3-benzothiazol-2-yl]urea

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

About 30 mg N-(6-cyano-1,3-benzothiazol-2-yl)-N′-ethylurea was charged into about 5 mL dry tetrahydrofuran. Added about 2 g of azidotributylstannane then refluxed for about 48–72 hours. The solvent was removed under reduced pressure then the crude oil was taken up in dichloromethane. About 0.5 mL of dilute aqueous hydrochloric acid was added and a white precipitate formed. This was allowed to sit for about 30 minutes then the precipitate was collected by filtration, washed with warm THF then dried under vacuum. 1H NMR 1.10 (t, 3H), 3.2 (m, 2H), 6.76 (br s, 1H), 7.78 (d, 1H), 8.0 (d, 1H), 8.58 (s, 1H), 10.91 (s, 1H); LC/MS 1.37 min, 290 (M+1).

후처리

  1. temperaturethen refluxed for about 48–72 hours
  2. customThe solvent was removed under reduced pressure
  3. additionAbout 0.5 mL of dilute aqueous hydrochloric acid was added
  4. customa white precipitate formed
  5. filtrationthe precipitate was collected by filtration
  6. washwashed with warm THF
  7. customthen dried under vacuum
  8. customLC/MS 1.37 min, 290 (M+1)

출처 및 근거

ORD 기록
ord-1c22368b0e704f58812f062c12896e4b
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091227B2

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