3-Bromo-4-fluoroaniline → N-(3-Bromo-4-fluorophenyl)-N′-(4-methyl-2-thiazolyl)urea

HRID 661881Notes

Reaction equation

HRID 661881 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[F:9])[NH2:5].[CH3:10][C:11]1[N:12]=[C:13]([NH:16][C:17](=O)[O:18]C2C=CC=CC=2)[S:14][CH:15]=1>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][C:17]([NH:16][C:13]2[S:14][CH:15]=[C:11]([CH3:10])[N:12]=2)=[O:18])[CH:6]=[CH:7][C:8]=1[F:9]

Participants

4

Reactant 2

HCID 27792863-Bromo-4-fluoroanilineHCID 59691744HCID 59691744, compound

Product 1

HCID 59375115N-(3-Bromo-4-fluorophenyl)-N′-(4-methyl-2-thiazolyl)urea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Step 2 A solution of 3-bromo-4-fluoroaniline (250 mg, 1.316 mmol) in THF (6 mL) was stirred on ice and treated with TEA (0.367 mL, 2.63 mmol), then with phenyl 4-methylthiazol-2-ylcarbamate (308 mg, 1.316 mmol) and the resulting solution was stirred at rt for 70 h. The mixture was concentrated and the residue was stirred in 1 M hydrochloric acid, forming a precipitate which was collected by filtration, rinsed with water and dried under vacuum to provide 1-(3-bromo-4-fluorophenyl)-3-(4-methylthiazol-2-yl)urea as an off white solid (400 mg, 92%). 1H NMR (400 MHz, DMSO-d6) δ 9.62 (s, 1H) 7.94 (dd, J=6.3, 2.5 Hz, 1H) 7.37-7.45 (m, 1H) 7.32 (t, J=8.7 Hz, 1H) 6.67 (d, J=1.1 Hz, 1H) 2.23 (d, J=1.1 Hz, 3H). Mass spectrum m/z 330, 332 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. customforming a precipitate which
  3. filtrationwas collected by filtration
  4. washrinsed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-7b620aba759d4566ae7ca383875f54de
Source dataset
uspto-grants-2011_12
Patent number
US08084620B2

Reaction notes

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