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

HRID 239891Notes

Reaction equation

HRID 239891 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, 2 H) 5.92 (s, 2 H) 7.11 (dd, J=7.3, 0.9 Hz, 1 H) 7.37 (d, J=8.5 Hz, 2 H) 7.46 (dd, J=8.5, 1.0 Hz, 1 H) 7.57 (d, J=8.5 Hz, 2 H) 7.57 (dd, J=8.1, 7.1 Hz, 1 H) 8.72 (s, 1 H) 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-9ccfae82a3d14eb2a5a54bc053bb65a7
Source dataset
uspto-grants-2014_02
Patent number
US08642776B2

Reaction notes

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