NaNCO → n-[4-(3-Amino-1,2-benzisoxazol-4-yl)phenyl]urea

HRID 1817741Notes

Reaction equation

HRID 1817741 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]3[C:14]([NH2:17])=[N:15][O:16][C:12]=3[CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[N-:18]=[C:19]=[O:20].[Na+]>CC(O)=O.O>[NH2:17][C:14]1[C:13]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:19]([NH2:18])=[O:20])=[CH:7][CH:6]=3)=[CH:9][CH:10]=[CH:11][C:12]=2[O:16][N:15]=1

Participants

5

Reactant 2

HCID 11051568NaNCOHCID 247683944-(4-Aminophenyl)-1,2-benzoxazol-3-amine

Product 1

HCID 11265647n-[4-(3-Amino-1,2-benzisoxazol-4-yl)phenyl]ureaYield 65.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

A solution of Example 261A (45 mg, 0.2 mmol) and sodium isocyanate (26 mg, 0.4 mmol) in HOAc (0.5 mL) and H2O (0.5 mL) was stirred overnight at rt, then diluted with water. The precipitated solid was collected by filtration and recrystallized from THF/hexanes to give an offwhite solid (35 mg, 65%). 1H NMR (300 MHz, DMSO-D6) δ ppm 5.20 (s, 2H) 5.92 (s, 2H) 7.11 (dd, J=7.3, 0.9 Hz, 1H) 7.37 (d, J=8.5 Hz, 2H) 7.46 (dd, J=8.5, 1.0 Hz, 1H) 7.57 (d, J=8.5 Hz, 2H) 7.57 (dd, J=8.1, 7.1 Hz, 1H) 8.72 (s, 1H) MS (ESI(+)) m/e 269.0 (M+H)+.

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. customrecrystallized from THF/hexanes

Sources & evidence

ORD record
ord-556fb1d56c03493980e3132d049d51af
Source dataset
uspto-grants-2009_10
Patent number
US07598283B2

Reaction notes

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