Ethyl orthopropionate → HCID 14851896, compound

HRID 1032750Notes

Reaction equation

HRID 1032750 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([I:19])[CH:17]=[CH:18][C:13]=2[N:12]=[C:11]([NH:20][NH2:21])[CH2:10][N:9]=1.[C:22](OCC)(OCC)(OCC)[CH2:23][CH3:24]>C1(C)C(C)=CC=CC=1>[CH2:23]([C:24]1[N:12]2[C:13]3[CH:18]=[CH:17][C:16]([I:19])=[CH:15][C:14]=3[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])=[N:9][CH2:10][C:11]2=[N:20][N:21]=1)[CH3:22]

Participants

4

Reactant 2

HCID 66995Ethyl orthopropionateHCID 14851834HCID 14851834, compound

Product 1

HCID 14851896HCID 14851896, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 1 g of 5-(2-fluorophenyl)-7-iodo-2-hydrazino-7-iodo-3H-1,4-benzodiazepine (see example 3), 5 ml of triethyl orthopropionate and 10 ml of xylene was heated to reflux for 1 hour. The solvents were partially distilled over and the residue was diluted with hexane. The precipitated crystals were collected and recrystallized from methanol/ethyl acetate to leave 1.05 g (97%) of 1-ethyl-6-(2-fluorophenyl)-8-iodo-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine with m.p. 209°-211° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 hour
  3. distillationThe solvents were partially distilled over and the residue
  4. additionwas diluted with hexane
  5. customThe precipitated crystals were collected
  6. customrecrystallized from methanol/ethyl acetate

Sources & evidence

ORD record
ord-15ef366a406445e09373b5dc6eb74de5
Source dataset
uspto-grants-1990_09
Patent number
US04959361

Reaction notes

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