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

HRID 9177Notes

Reaction equation

HRID 9177 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([CH2:11]C#N)[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH2:14]([N:16]=[C:17]=[O:18])[CH3:15].[CH2:19]([N:21](CC)CC)C>CN(C)C=O>[CH3:11][C:9]1[CH:8]=[C:7]([C:19]#[N:21])[C:5]2[N:6]=[C:2]([NH:1][C:17]([NH:16][CH2:14][CH3:15])=[O:18])[S:3][C:4]=2[CH:10]=1

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 21298164(2-Amino-1,3-benzothiazol-6-yl)acetonitrile

Product 1

HCID 21985550N-(6-Methylcyano-1,3-benzothiazol-2-yl)-N'-ethylurea

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

About 1 g of (2-amino-1,3-benzothiazol-6-yl)methyl cyanide is dissolved in about 10 ml dimethylformamide. About 0.8 ml of ethylisocyanate is added followed by about 1.4 ml triethylamine and the solution is heated to about 80° C. under good agitation. The solution is allowed to stir for about 4–6 hours then cooled to RT. The solvent is removed in vacuo and the solids are washed well with ether. The product is recrystallized from hot EtOAc. 1H NMR 1.09 (t, 3H), 3.1 (m, 2H), 4.1 (s, 2H), 6.72 (m, 1H), 7.32 (m, 1H), 7.61 (d, 1H), 7.85 (s, 1H), 10.7 (s, 1H); LC/MS 2.73 min, 261 (M+1), 259 (M−1).

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 recrystallized from hot EtOAc
  5. customLC/MS 2.73 min, 261 (M+1), 259 (M−1)

Sources & evidence

ORD record
ord-157697f4a0e64340ac2d0e8d298b748a
Source dataset
uspto-grants-2006_08
Patent number
US07091227B2

Reaction notes

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