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

HRID 9175

Reaction equation

HRID 9175 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-1c22368b0e704f58812f062c12896e4b
Source dataset
uspto-grants-2006_08
Patent number
US07091227B2

Linked notes

Loading…