Potassium Bromide → HCID 20394580, compound

HRID 26058Notes

Reaction equation

HRID 26058 reaction equation
[Cl: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]([Cl:19])[CH:17]=[CH:18][C:13]=2[N:12]2[C:20](Cl)=[N:21][C:22]([C:23]([NH2:25])=[O:24])=[C:11]2[CH2:10][N:9]=1.[CH3:27][O-:28].[Na+].[K+].[Br-]>CO>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]2[N:12]3[C:20]([O:28][CH3:27])=[N:21][C:22]([C:23]([NH2:25])=[O:24])=[C:11]3[CH2:10][N:9]=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[C:14]=2[CH:15]=1

Participants

5

Reactant 3

HCID 253877Potassium BromideHCID 10942334Sodium MethoxideHCID 203945796-(2-chlorophenyl)-1,8-dichloro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxamide

Product 1

HCID 20394580HCID 20394580, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 0.3 g (0.00074 mole) of 6-(2-chlorophenyl)-1,8-dichloro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxamide, 1.15 g (0.0028 mole) of sodium methoxide and 15 ml of methanol was heated at 120°-125° in a steel bomb for 24 hrs. The solvent was evaporated in vacuo. The residue was dissolved in methylene chloride, washed with water, dried and evaporated at reduced pressure to give a tan, amorphous solid. After chromatography over silica gel using 5% (v/v) of ethanol in methylene chloride the solid was recrystallized from a solution of ethanol and methylene chloride to give off-white crystals with mp 235°-238° (dec.). Uv λ max 216 mμ (ε=41,000) sh 243 (22,600) max 264 (20,000); ir (KBr) 3445, 3330, 3280 cm-1 (NH2) 1675 (CON) nmr (d-DMSO) δ 4.0 ppm (d, 1) and 5.88 (d, 1) (AB-system, J=12 Hz, C4 -H) 4.06 (s, 3, OCH3) 6.9-7.9 (m, 9, aromatic H and NH2).

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionThe residue was dissolved in methylene chloride
  3. washwashed with water
  4. customdried
  5. customevaporated at reduced pressure
  6. customto give a tan, amorphous solid
  7. customAfter chromatography over silica gel using 5% (v/v) of ethanol in methylene chloride the solid was recrystallized from a solution of ethanol and methylene chloride
  8. customto give off-white crystals with mp 235°-238° (dec.)

Sources & evidence

ORD record
ord-42ab6fef30e742b2b54ce6d88a3a9cd9
Source dataset
uspto-grants-1979_04
Patent number
US04147875

Reaction notes

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