Water → HCID 15702796, compound

HRID 2073199Notes

Reaction equation

HRID 2073199 reaction equation
[NH2:1][C:2]1[N:12]2[C:13]3[N:8]([C:9]([C:14]4[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=4)=[CH:10][CH2:11]2)[N:7]=[CH:6][C:5]=3[C:4](=[O:24])[N:3]=1.CN(C1C2C(N(C)C)=CC=CC=2C=CC=1)C.[Cl:41][CH2:42][C:43](Cl)=[O:44].O>O1CCCC1>[Cl:41][CH2:42][C:43]([NH:1][C:2]1[N:12]2[C:13]3[N:8]([C:9]([C:14]4[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=4)=[CH:10][CH2:11]2)[N:7]=[CH:6][C:5]=3[C:4](=[O:24])[N:3]=1)=[O:44]

Participants

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 88675Proton spongeHCID 9905671HCID 9905671, compound

Product 1

HCID 15702796HCID 15702796, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 500 mg amount of 5-amino-8-[3-(trifuoromethyl)phenyl]-3H,6H-1,4,5a,8a-tetraazaacenaphthylen-3-one (prepared as described in Example 29) was suspended and stirred in 30 ml of dry tetrahydrofuran, then 1 equivalent (0.322 g) of [1,8-bis(dimethylamino)-naphthalene,N,N,N',N'-tetramethyl-1,8-naphthalenediamine] (Proton Sponge® was added followed by 1.1 equivalents (0.187 g) of chloroacetyl chloride. The reaction mixture was heated at reflux for 16 hours, then allowed to cool to room temperature. The mixture was poured into 200 ml of water and the resulting precipitate was collected by filtration to give 423 mg of the product of the example as a brown solid, m.p. 189°-192° C. (dec).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 16 hours
  3. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-003481090dfb44a28aef4ca2799d434a
Source dataset
uspto-grants-1990_04
Patent number
US04916137

Reaction notes

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