Sodium Hydroxide → N1,N1-dimethyl-2-oxazol-2-yl-benzene-1,4-diamine

HRID 450101Notes

Reaction equation

HRID 450101 reaction equation
[CH3:1][N:2]([CH3:17])[C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[CH:5][C:4]=1[C:12]1[O:13][CH:14]=[CH:15][N:16]=1.[OH-].[Na+]>C(O)(=O)C.[Fe]>[CH3:1][N:2]([CH3:17])[C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][C:4]=1[C:12]1[O:13][CH:14]=[CH:15][N:16]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68827592Dimethyl-(4-nitro-2-oxazol-2-yl-phenyl)-amine

Product 1

HCID 68826585N1,N1-dimethyl-2-oxazol-2-yl-benzene-1,4-diamineYield 88.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

Iron powder (0.15 g, 2.574 mmol) was added to a solution of dimethyl-(4-nitro-2-oxazol-2-yl-phenyl)-amine (200 mg, 0.86 mmol) in acetic acid (3 ml) and stirred overnight at room temperature. The reaction mixture was poured into ice water and basified with dilute sodium hydroxide solution and then filtered. The filtrate was extracted with ethyl acetate, and the organic layer was washed with water, then brine and dried. Evaporation to dryness gave N1,N1-dimethyl-2-oxazol-2-yl-benzene-1,4-diamine (150 mg, 88.2%) as oil.

Workup

  1. filtrationfiltered
  2. extractionThe filtrate was extracted with ethyl acetate
  3. washthe organic layer was washed with water
  4. dry with materialbrine and dried
  5. customEvaporation to dryness

Sources & evidence

ORD record
ord-8db61f2ba02b48d4b54cf462e15b3c09
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

Loading…