Formamide → HCID 14590422, compound

HRID 651570Notes

Reaction equation

HRID 651570 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:22])[N:9]([CH3:21])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16](OCC)=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.C([NH2:25])=O.C[O-].[Na+].O>O1CCOCC1>[Cl:1][C:2]1[C:7]2[C:8](=[O:22])[N:9]([CH3:21])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([NH2:25])=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 713FormamideHCID 962WaterHCID 71231SarmazenilHCID 10942334Sodium Methoxide

Product 1

HCID 14590422HCID 14590422, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

22.8 g Ethyl 7-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]-benzodiazepine-3-carboxylate were suspended under stirring and argon atmosphere in 91.2 ml 1,4-dioxane. 14.1 ml Formamide and 13.9 ml sodium methanolate were successively added to yield a clear light-orange solution, which turned to a white suspension after 10 minutes. This suspension was stirred two hours at 30° C. 200 ml Deionized water were added in one portion and 1,4-dioxane was distilled off at 40° C. under reduced pressure. The remaining white suspension was stirred two hours at 0° C. and filtered. The precipitate (7-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxamide) was washed with 50 ml deionized water three times and dried under reduced pressure for 18 hours at 80° C. Crude product:19.43 g as a white powder. m.p. >250° C.

Workup

  1. customto yield a clear light-orange solution, which
  2. stirringThis suspension was stirred two hours at 30° C
  3. distillationwas distilled off at 40° C. under reduced pressure
  4. stirringThe remaining white suspension was stirred two hours at 0° C.
  5. filtrationfiltered
  6. washThe precipitate (7-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxamide) was washed with 50 ml
  7. customdried under reduced pressure for 18 hours at 80° C

Sources & evidence

ORD record
ord-511484f7f5014ef5b36beb7d1bb1b2c1
Source dataset
uspto-grants-2001_08
Patent number
US06281353B1

Reaction notes

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