Dimethylformamide → N-(6-Cyano-1,3-benzothiazol-2-yl)-N'-ethylurea

HRID 9101Notes

Reaction equation

HRID 9101 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([C:11]#[N:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH2:13]([N:15]([CH2:18]C)CC)[CH3:14].CN(C)C=[O:23]>>[C:11]([C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([NH:1][C:18]([NH:15][CH2:13][CH3:14])=[O:23])[S:3][C:4]=2[CH:10]=1)#[N:12]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 43271392-Aminobenzothiazole-6-carbonitrile

Product 1

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

Conditions

Temperature
80 °C

Procedure

2-Amino-1,3-benzothiazole-6-carbonitrile is dissolved in a polar aprotic solvent, preferrably dimethylformamide. R3NCO is added, followed by an alkyl amine base, preferably triethylamine and the solution is heated to about 70–90° C., preferably about 80° C., under good agitation. The solution is allowed to stir for about 4–8 hours, preferably about 4 hours, then cooled to room temperature. The solvent is removed in vacuo and the solids are washed well with ether. The product is further purified by column chromatography and after drying in vacuo, the title product is isolated.

Workup

  1. temperaturecooled to room temperature
  2. customThe solvent is removed in vacuo
  3. washthe solids are washed well with ether
  4. customThe product is further purified by column chromatography
  5. customafter drying in vacuo

Sources & evidence

ORD record
ord-0c848bca2734433db737a84e3267c158
Source dataset
uspto-grants-2006_08
Patent number
US07091227B2

Reaction notes

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