5-Isocyanato-1,3-dioxaindane → 1-Benzo[1,3]dioxol-5-yl-3-(4-benzoxazol-2-yl-pyridin-2-yl)-urea

HRID 1697170Notes

Reaction equation

HRID 1697170 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:15]=[CH:14][N:13]=[C:12]([NH2:16])[CH:11]=1.[CH2:17]1[O:25][C:24]2[CH:23]=[CH:22][C:21]([N:26]=[C:27]=[O:28])=[CH:20][C:19]=2[O:18]1>N1C=CC=CC=1>[O:25]1[C:24]2[CH:23]=[CH:22][C:21]([NH:26][C:27]([NH:16][C:12]3[CH:11]=[C:10]([C:2]4[O:1][C:5]5[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=5[N:3]=4)[CH:15]=[CH:14][N:13]=3)=[O:28])=[CH:20][C:19]=2[O:18][CH2:17]1

Participants

4

Reactant 2

HCID 52232135-Isocyanato-1,3-dioxaindaneHCID 596799644-Benzoxazol-2-yl-pyridin-2-ylamine

Product 1

HCID 596799911-Benzo[1,3]dioxol-5-yl-3-(4-benzoxazol-2-yl-pyridin-2-yl)-urea

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A microwave vial was charged with 4-benzoxazol-2-yl-pyridin-2-ylamine (0.05 g, 0.2 mmol), 3,4-(methylenedioxy)phenyl isocyanate (0.04 g, 0.2 mmol) and 1 mL of pyridine. The mixture was subjected to microwave irradiation at 160° C. for 15 minutes. Upon cooling, a precipitate formed. The solid was filtered and then triturated with hot methanol. The undissolved material was filtered, and the precipitate that formed in the mother liquor was filtered and dried to afford the desired product as a white solid. (Calc'd for C20H14N4O4: 374.36, [M+H]+ found: 375.1).

Workup

  1. customirradiation at 160° C. for 15 minutes
  2. temperatureUpon cooling
  3. customa precipitate formed
  4. filtrationThe solid was filtered
  5. customtriturated with hot methanol
  6. filtrationThe undissolved material was filtered
  7. customthe precipitate that formed in the mother liquor
  8. filtrationwas filtered
  9. customdried

Sources & evidence

ORD record
ord-95fd6aff18874de79a9ca7ca53669bda
Source dataset
uspto-grants-2012_04
Patent number
US08163908B2

Reaction notes

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