2,2,2-Trichloroethyl chloroformate → HCID 15702797, compound

HRID 2073200Notes

Reaction equation

HRID 2073200 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[C:42]([O:44][CH2:45][C:46]([Cl:49])([Cl:48])[Cl:47])=[O:43]>O1CCCC1>[O:24]=[C:4]1[N:3]=[C:2]([NH:1][C:42](=[O:43])[O:44][CH2:45][C:46]([Cl:49])([Cl:48])[Cl:47])[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]1=3

Participants

5

Reactant 3

HCID 870632,2,2-Trichloroethyl chloroformateHCID 88675Proton spongeHCID 9905671HCID 9905671, compound

Product 1

HCID 15702797HCID 15702797, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 500 mg amount of 5-amino-8-[3-(trifluoromethyl)phenyl]-3H,6H-1,4,5a,8a-tetraazaacenaphthylen-3-one (prepared as described in Example 29) was suspended and stirred in 25.0 ml of dry tetrahydrofuran, then 320 mg of [1,8-bis(dimethylamino)naphthalene,N,N, N',N'-tetramethyl-1,8-naphthalenediamine] (Proton Sponge®) was added followed by 0.207 ml of 2,2,2-trichloroethyl chloroformate. This mixture was heated at reflux for 16 hours. The reaction mixture was quenched by pouring it into 200 ml of water and the precipitate formed was collected by filtration to give 419 mg of the desired product as a white solid, m.p. 225°-226° C.

Workup

  1. temperatureThis mixture was heated
  2. temperatureat reflux for 16 hours
  3. customThe reaction mixture was quenched
  4. additionby pouring it into 200 ml of water
  5. customthe precipitate formed
  6. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-b0a4f20a42de4c2690c81d20afa9a520
Source dataset
uspto-grants-1990_04
Patent number
US04916137

Reaction notes

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