5-amino-2H-1,3-benzodiazol-2-one → HCID 178517074, compound

HRID 1063386Notes

Reaction equation

HRID 1063386 reaction equation
O[CH:2]=[C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:12].[NH2:13][C:14]1[CH:23]=[CH:22][C:17]2=[N:18][C:19](=[O:21])[N:20]=[C:16]2[CH:15]=1>C(O)C>[O:12]=[C:4]1[NH:5][C:6]2[C:11](/[C:3]/1=[CH:2]/[NH:13][C:14]1[CH:23]=[CH:22][C:17]3[NH:18][C:19](=[O:21])[NH:20][C:16]=3[CH:15]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

4

Reactant 2

HCID 152505475-amino-2H-1,3-benzodiazol-2-oneHCID 1784187413-(hydroxymethylidene)-1H-indol-2-one

Product 1

HCID 178517074HCID 178517074, compoundYield 51.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 161 mg (1.00 mMol) of 3-(hydroxymethylene)-1,3-dihydro-2H-indol-2-one, 149 mg (1.00 mMol) of 5-aminobenzimidazolone, and 5 ml of ethanol was heated at 55° C. for 1.5 hr. The resulting solid was isolated by filtration and recrystallized from DMSO/methanol to yield 150 mg (51%) of a yellow solid, 1H NMR (DMSO-d6): δ6.80 (d, J=7.7 Hz, 1H), 6.85-6.98 (m, 4H), 7.00 (s, 1H), 7.54 (d, J=7.4 Hz, 1H), 8.50 (d, J=12.7 Hz, 1H), 10.39 (s, 1H), 10.56 (s, 1H), 10.72 (d, J=12.7 Hz, 1H), 10.74 (s, 1H); APCI-MS m/z291 (M−H)−.

Workup

  1. customThe resulting solid was isolated by filtration
  2. customrecrystallized from DMSO/methanol

Sources & evidence

ORD record
ord-4a6d7647c36d4a0fbe05714369f37369
Source dataset
uspto-grants-2005_11
Patent number
US06964977B2

Reaction notes

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