Methanol → HCID 86680405, compound

HRID 1023164Notes

Reaction equation

HRID 1023164 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[O:11][C:12]([CH2:15][O:16][C:17]3[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=3)=[N:13][N:14]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].CO.[Cl-].[NH4+]>O.[Fe]>[NH2:23][C:20]1[CH:21]=[CH:22][C:17]([O:16][CH2:15][C:12]2[O:11][C:10]([NH:9][C:4]3[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=3)=[N:14][N:13]=2)=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 86680406HCID 86680406, compound

Product 1

HCID 86680405HCID 86680405, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

To a stirred solution of N-(3,4-dichlorophenyl)-5-((4-nitrophenoxy)methyl)-1,3,4-oxadiazol-2-amine (150 mg, 0.394 mmol) in water (20 mL)/methanol (20 mL), ammonium chloride (211 mg, 3.94 mmol) and iron powder (176 mg, 3.15 mmol) were added and heated to reflux for 4 hours. The reaction mixture was passed though Celite. Solvent was removed under vacuum to obtain 5-((4-aminophenoxy)methyl)-N-(3,4-dichlorophenyl)-1,3,4-oxadiazol-2-amine (0.12 g, 87%). 1H NMR: 400 MHZ, DMSO-d6: δ 5.16 (s, 2H), 5.60 (bs, 2H), 6.62 (d, J=8.40 Hz, 2H), 6.82 (dd, J=2.00, 6.80 Hz, 2H), 7.48 (dd, J=2.40, 8.80 Hz, 1H), 7.61 (d, J=8.80 Hz, 1H), 7.89 (d, J=2.80 Hz, 1H), 11.00 (s, 1H). LCMS: RT 1.66 min. LCMS (ES-API), m/z 351.0 (M+H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 hours
  3. customSolvent was removed under vacuum

Sources & evidence

ORD record
ord-ff1faa3900b845399f0560b8017fd20f
Source dataset
uspto-grants-2014_05
Patent number
US08722670B2

Reaction notes

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