Ethanol → 5-[(1-Methylethyl)amino]-8-[3-(trifluoromethyl)-phenyl]-3H,6H-1,4,5a,8a-tetraazaacenaphthylen-3-one

HRID 6219

Reaction equation

HRID 6219 reaction equation
CS[C:3]1[N:13]2[C:14]3[N:9]([C:10]([C:15]4[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=4)=[CH:11][CH2:12]2)[N:8]=[CH:7][C:6]=3[C:5](=[O:25])[N:4]=1.[CH:26]([NH2:29])([CH3:28])[CH3:27].C(O)C>C(O)(=O)C>[CH3:27][CH:26]([NH:29][C:3]1[N:13]2[C:14]3[N:9]([C:10]([C:15]4[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:23])([F:24])[F:22])[CH:16]=4)=[CH:11][CH2:12]2)[N:8]=[CH:7][C:6]=3[C:5](=[O:25])[N:4]=1)[CH3:28]

Participants

5

Reactant 3

HCID 702Ethanol2×HCID 6363IsopropylamineHCID 98853995-(Methylthio)-8-(3-(trifluoromethyl)phenyl)-3H,6H-1,4,5a,8a-tetraazaacenaphthylen-3-one

Product 1

HCID 150440865-[(1-Methylethyl)amino]-8-[3-(trifluoromethyl)-phenyl]-3H,6H-1,4,5a,8a-tetraazaacenaphthylen-3-oneYield 62.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a suspension of 5.0 g of 5-(methylthio)-8-[3-(trifluoromethyl)phenyl]-3H,6H-1,4,5a,8a-tetraazaacenaphthylen-3-one in 35 ml of acetic acid is added 2.64 g of isopropylamine. The reaction mixture is heated on a steambath for 18 hours. The resulting solution is cooled to room temperature and 17 ml of ethanol added. The mixture is cooled to 10° C. and 35 ml of ethanol and 20 g of ice added. The mixture is stirred for an additional 30 minutes at -10° C. The product is collected by filtration, washed with ethanol (2×20 ml) and air-dried to give 3.2 g (62.3%) of the desired product.

Workup

  1. temperatureThe reaction mixture is heated on a steambath for 18 hours
  2. temperatureThe mixture is cooled to 10° C.
  3. filtrationThe product is collected by filtration
  4. washwashed with ethanol (2×20 ml)
  5. customair-dried

Sources & evidence

ORD record
ord-eadcefa2a05d42d58610fc3268716e7a
Source dataset
uspto-grants-1993_09
Patent number
US05247086

Linked notes

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