Toluene → HCID 19438789, compound

HRID 1733873Notes

Reaction equation

HRID 1733873 reaction equation
[C:1]([Cl:4])(Cl)=O.C1(C)C=CC=CC=1.[CH2:12]([O:19][N:20]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([N:30]3[CH:34]=[CH:33][N:32]=[CH:31]3)[CH:28]=2)[NH:23]C(=O)[C:21]1=[O:36])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C)C=O>[CH2:12]([O:19][N:20]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([N:30]3[CH:34]=[CH:33][N:32]=[CH:31]3)[CH:28]=2)[N:23]=[C:1]([Cl:4])[C:21]1=[O:36])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6371PhosgeneHCID 19438766HCID 19438766, compound

Product 1

HCID 19438789HCID 19438789, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 20% phosgene in toluene (57 ml; 118 mmol) was added to a stirred solution of 4-benzyloxy-6-(1H-imidazol-1-yl)-quinoxaline-2,3(1H,4H)-dione (9.2 g; 27.5 mmol) in 200 ml dry N,N-dimethylformamide at 0° C. The mixture was stirred at 25° C. overnight and then evaporated in vacuo. The residue was stirred with ice-cooled water and 4N sodium hydroxide was added until pH was about 6 which resulted in the title compound (9.5 g; 98%) as a precipitate. M.p. 140° C. (decomp.).

Workup

  1. customevaporated in vacuo
  2. stirringThe residue was stirred with ice-
  3. temperaturecooled water and 4N sodium hydroxide
  4. additionwas added until pH was about 6 which

Sources & evidence

ORD record
ord-10cc1b549f8343e4bb20b22f16fbb082
Source dataset
uspto-grants-1996_07
Patent number
US05532236

Reaction notes

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