Ethyl isocyanate → 1-(6-Bromo-2-benzothiazolyl)-3-ethylurea

HRID 9171

Reaction equation

HRID 9171 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([NH2:9])[S:8][C:4]=2[CH:3]=1.[CH2:12]([N:14]=[C:15]=[O:16])[CH3:13].C(N(CC)CC)C>CN(C=O)C>[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([NH:9][C:15]([NH:14][CH2:12][CH3:13])=[O:16])[S:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 851492-Benzothiazolamine, 6-bromo-

Product 1

HCID 219855641-(6-Bromo-2-benzothiazolyl)-3-ethylurea

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

About 0.75 g of 6-bromo-1,3-benzothiazol-2-amine (crude) is dissolved in about 15 mL DMF. About 0.5 mL of ethylisocyanate is added followed by about 0.9 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.

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

Sources & evidence

ORD record
ord-0c31608d9ad04d16b80f61e52ee18c38
Source dataset
uspto-grants-2006_08
Patent number
US07091227B2

Linked notes

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