Acetone → 9H-xanthene-9-carboxylic acid (5-ethyl-[1,3,4]oxadiazol-2-yl)amide

HRID 392725Notes

Reaction equation

HRID 392725 reaction equation
CC1C=C(C)N([C:8]([CH:10]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[O:17][C:16]3[C:11]2=[CH:12][CH:13]=[CH:14][CH:15]=3)=[O:9])N=1.[CH2:24]([C:26]1[O:30][C:29]([NH2:31])=[N:28][N:27]=1)[CH3:25].CC(C)=O>CN(C=O)C>[CH2:24]([C:26]1[O:30][C:29]([NH:31][C:8]([CH:10]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=3[O:17][C:18]3[C:23]2=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:9])=[N:28][N:27]=1)[CH3:25]

Participants

5

Reactant 3

HCID 180AcetoneHCID 3434875-Ethyl-1,3,4-oxadiazol-2-amineHCID 4521579(3,5-dimethylpyrazol-1-yl)-(9H-xanthen-9-yl)methanone

Product 1

HCID 539225629H-xanthene-9-carboxylic acid (5-ethyl-[1,3,4]oxadiazol-2-yl)amideYield 41.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

500.5 mg (1.64 mmol) (3,5-dimethylpyrazol-1-yl)-(9H-xanthen-9-yl)methanone and 186.8 mg (1.64 mmol) 5-ethyl-[1,3,4]oxadiazol-2-ylamine were suspended in 1.5 ml DMF and stirred for 6 h at 130°. The reaction mixture was allowed to cool to room temperature and 5 ml of acetone were added. After stirring for 5 min, the product was filtered, washed with acetone and dried in vaccuo to yield 219.5 mg of 9H-xanthene-9-carboxylic acid (5-ethyl-[1,3,4]oxadiazol-2-yl)amide as a white solid, m.p. 256-257° C. and MS: m/e=321.2 (M+)

Workup

  1. stirringAfter stirring for 5 min
  2. filtrationthe product was filtered
  3. washwashed with acetone
  4. customdried in vaccuo

Sources & evidence

ORD record
ord-c3104af2814744f68d1c04bda2302a0b
Source dataset
uspto-grants-2004_10
Patent number
US06803381B1

Reaction notes

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