Hydrochloric Acid → HCID 53919645, compound

HRID 1982389Notes

Reaction equation

HRID 1982389 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]2[CH2:6][N:7]3[CH:14]=[CH:13][CH:12]=[C:8]3[C:9](=[O:11])[NH:10][C:4]=2[CH:3]=1.[Cl-].[Cl-].[Cl-].[Al+3].[CH3:21]I.Cl>C(Cl)Cl.CO>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]2[CH2:6][N:7]3[CH:14]=[C:13]([CH3:21])[CH:12]=[C:8]3[C:9](=[O:11])[NH:10][C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 6451240Aluminum(III) ChlorideHCID 12595984HCID 12595984, compound

Product 1

HCID 53919645HCID 53919645, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2.33 g of 8-chloro-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-11-one in 50 mL of methylene chloride is added 5.33 g of aluminum trichloride in small aliquots over a 30 minute period. During this time the temperature of the reaction is maintained below 30°. To this reaction mixture 4 mL of methyl iodide is added, and the reaction is allowed to stir for 48 hours at room temperature. The reaction mixture is diluted with 24 mL of methanol and then poured into 150 mL of dilute hydrochloric acid. The methylene chloride layer is separated and washed with 200 mL of brine and saturated aqueous sodium bicarbonate. The methylene chloride extract is dried over anhydrous magnesium sulfate and evaporated to dryness to yield 8-chloro-2-methyl-10,11-dihydro-5-H-pyrrolo-[2,1-c][1,4]benzodiazepine-11-one, which was used without further purification.

Workup

  1. temperatureDuring this time the temperature of the reaction is maintained below 30°
  2. customThe methylene chloride layer is separated
  3. washwashed with 200 mL of brine and saturated aqueous sodium bicarbonate
  4. extractionThe methylene chloride extract
  5. dry with materialis dried over anhydrous magnesium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-c9979adaa56a43c18a97743c9ff0386f
Source dataset
uspto-grants-1986_06
Patent number
US04596799

Reaction notes

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