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

HRID 1430389Notes

Reaction equation

HRID 1430389 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 off white 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-f1fac77a40824dd4b96fd4565543b74b
Source dataset
uspto-grants-2015_01
Patent number
US08940778B2

Reaction notes

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