Water → HCID 14951370, compound

HRID 2211188Notes

Reaction equation

HRID 2211188 reaction equation
CS([C:5]1[O:9][C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=2)=[N:7][N:6]=1)(=O)=O.O.[N:28]#[C:29][NH2:30].C(N(CC)CC)C>CN(C)C=O.CCOCC>[F:24][C:23]([F:26])([F:25])[C:19]1[CH:18]=[C:17]([NH:16][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:8]2[O:9][C:5]([NH:30][C:29]#[N:28])=[N:6][N:7]=2)[CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 9864Cyanamide2×HCID 14951369HCID 14951369, compound

Product 1

HCID 14951370HCID 14951370, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To an ambient solution of N-[2-[5-(methylsulfonyl)-1,3,4-oxadiazol-2-yl]phenyl]-3-trifluoromethyl benzenamine (210.4 mg, 0.549 mmoles) in 5 ml of dimethylformamide is added 1 ml of water followed by cyanamide (196.0 mg, 4.66 mmoles) and triethylamine (100 μl, 0.717 mmoles). The reaction mixture is stirred at 80° C. overnight. An additional amount of cyanamide (96 mg) is added, and heating is continued for six hours. The mixture is poured into ether and extracted into 0.3N sodium hydroxide. The aqueous layer is acidified with 1N hydrochloric acid, and the resulting white solid is collected by filtration, washing with water. Recrystallization from acetonitrile provides 95.8 mg (51%) of 5-[2-[[3-(trifluoromethyl)phenyl]amino]phenyl]-1,3,4-oxadiazol-2-yl-cyanamide, mp above 230° C.

Workup

  1. temperatureheating
  2. waitis continued for six hours
  3. extractionextracted into 0.3N sodium hydroxide
  4. filtrationthe resulting white solid is collected by filtration
  5. washwashing with water
  6. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-d54a536b96e44f428e6bb0525dccbaf1
Source dataset
uspto-grants-1995_10
Patent number
US05462952

Reaction notes

Loading…