Water → 1-(5-Bromo-6-fluoro-benzothiazol-2-yl)-3-ethyl-urea

HRID 2068686Notes

Reaction equation

HRID 2068686 reaction equation
[Br:1][C:2]1[C:3]([F:12])=[CH:4][C:5]2[S:9][C:8]([NH2:10])=[N:7][C:6]=2[CH:11]=1.[CH2:13]([N:15]=[C:16]=[O:17])[CH3:14].O>O1CCOCC1>[Br:1][C:2]1[C:3]([F:12])=[CH:4][C:5]2[S:9][C:8]([NH:10][C:16]([NH:15][CH2:13][CH3:14])=[O:17])=[N:7][C:6]=2[CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8022Ethyl isocyanateHCID 596030945-Bromo-6-fluorobenzo[d]thiazol-2-amine

Product 1

HCID 596030721-(5-Bromo-6-fluoro-benzothiazol-2-yl)-3-ethyl-ureaYield 69%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-bromo-6-fluoro-benzothiazol-2-ylamine IV (0.36 g, 1.45 mmol) in 1,4-dioxane (25.0 mL) was added ethyl isocyanate (0.69 mL, 8.74 mmol) and the resulting reaction mixture was heated at 80° C. for 15 h. After the completion of the reaction (TLC monitoring) the solvent was evaporated. The residue thus obtained was stirred with water at 60° C. for 5 h. The solution was then filtered and washed with ether to get the title compound (0.30 g, 69%). 1H-NMR (400 MHz, DMSO-d6): δ 1.08 (t, J=6.80 Hz, 3H), 3.17 (m, 2H), 6.69 (br s, 1H), 7.92 (d, J=6.40 Hz, 1H), 8.0 (d, J=8.40 Hz, 1H) and 10.86 (br s, 1H).

Workup

  1. customthe resulting reaction mixture
  2. customAfter the completion of the reaction (TLC monitoring) the solvent
  3. customwas evaporated
  4. customThe residue thus obtained
  5. filtrationThe solution was then filtered
  6. washwashed with ether

Sources & evidence

ORD record
ord-b62c76bae14d4bb7aef4b218c6e544f0
Source dataset
uspto-grants-2012_10
Patent number
US08299065B2

Reaction notes

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