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].Cl.NO.C(=O)([O-])[O-:22].[Na+].[Na+]>>[CH2:14]([NH:13][C:11]([NH:10][C:8]1[S:9][C:5]2[CH:4]=[C:3]([C:1]([NH2:2])=[O:22])[CH:17]=[CH:16][C:6]=2[N:7]=1)=[O:12])[CH3:15]Participants
4
Procedure
About 1 g of N-(6-cyano-1,3-benzothiazol-2-yl)-N′-ethylurea was charged into about 30 mL of aqueous alkanol. Added about 0.6 g hydroxylamine hydrochloride and about 0.45 g sodium carbonate then heated to reflux. The solution was refluxed for about 4–8 hours then cooled to room temperature. The precipitate was recovered by filtration and washed well with water. LC/MS indicated a mixture of two products identified as the following after further purification by preparative HPLC:
Workup
- temperaturethen heated to reflux
- temperatureThe solution was refluxed for about 4–8 hours
- filtrationThe precipitate was recovered by filtration
- washwashed well with water
- additiona mixture of two products
- customfollowing after further purification by preparative HPLC
Sources & evidence
- ORD record
- ord-42e183c75b274ca58d1e4a2d590f020c
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07091227B2
Linked notes
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