6-Chloro-2-benzothiazolamine → N-(6-Chloro-1,3-benzothiazol-2-yl)-N'-ethylurea

HRID 9098

Reaction equation

HRID 9098 reaction equation
[Cl: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>[Cl: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 72266-Chloro-2-benzothiazolamineHCID 8022Ethyl isocyanateHCID 8471Triethylamine

Product 1

HCID 9964976N-(6-Chloro-1,3-benzothiazol-2-yl)-N'-ethylurea

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Three grams of 6-chloro-1,3-benzothiazol-2-amine was dissolved in about 50 mL DMF. Next, about 2.5 mL of EtNCO was added followed by about 3.2 mL of triethylamine. The solution was allowed to react at about 80° C. for about 8 hours. The reaction solvent was then removed in vacuo and the crude oil was taken up in ether. The solids were isolated by filtration and washed with ether. The product was then dried in vacuo. 1H NMR 1.09 (t, 3H, J=7.2 Hz), 3.19 (m, 2H), 6.74 (br s, 1H), 7.37 (d, 1H, J=8.58 Hz), 7.60 (d, 1H, J=8.59 Hz), 8.01 (s, 1H), 10.8 (br s, 1H). LCMS: R.T. 2.3 min, MH-254 m/z.

Workup

  1. customto react at about 80° C. for about 8 hours
  2. customThe reaction solvent was then removed in vacuo
  3. customThe solids were isolated by filtration
  4. washwashed with ether
  5. customThe product was then dried in vacuo

Sources & evidence

ORD record
ord-68f4737b6c484d558c81c99a24e5ed31
Source dataset
uspto-grants-2006_08
Patent number
US07091227B2

Linked notes

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