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

HRID 9168

Reaction equation

HRID 9168 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]=[C:16]=[O:17])[CH3:14].C(N(CC)CC)C>CN(C)C=O>[C:11]([C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([NH:1][C:16]([NH:15][CH2:13][CH3:14])=[O:17])[S:3][C:4]=2[CH:10]=1)#[N:12]

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 43271392-Aminobenzothiazole-6-carbonitrile

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

0.2 grams of 2-amino-1,3-benzothiazole-6-carbonitrile is dissolved in about 5 ml dimethylformamide. About 0.2 ml of ethylisocyanate is added followed by about 0.3 ml triethylamine and the solution is heated to about 80° C. under good agitation. The solution is allowed to stir for about 4 hours then cooled to RT. 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, about 0.14 grams is isolated.

Workup

  1. temperaturethen cooled to RT
  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
  6. customabout 0.14 grams is isolated

Sources & evidence

ORD record
ord-b5781a6f057c43938316f29e4db42aaf
Source dataset
uspto-grants-2006_08
Patent number
US07091227B2

Linked notes

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