Dichloromethane → HCID 23316355, compound

HRID 1982390Notes

Reaction equation

HRID 1982390 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[CH2:6][N:7]3[CH:14]=[C:13]([CH3:15])[CH:12]=[C:8]3[C:9](=O)[NH:10][C:4]=2[CH:3]=1.P(Cl)(Cl)([Cl:20])=O.C(Cl)Cl.C(=O)([O-])[O-].[Na+].[Na+]>ClC1C=CC=CC=1>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[CH2:6][N:7]3[CH:14]=[C:13]([CH3:15])[CH:12]=[C:8]3[C:9]([Cl:20])=[N:10][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 53919645HCID 53919645, compound

Product 1

HCID 23316355HCID 23316355, compound

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

To a suspension of 1.1 g of 8-chloro-2-methyl-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-11-one in 20 mL of chlorobenzene is added 680 mg of phosphorous oxychloride. The mixture is heated at 100°-110° for 1 hour, then allowed to cool to room temperature. Methylene chloride (150 mL) is added to the stirred reaction mixture which is then poured into a mixture of ice and aqueous sodium carbonate. After being shaken vigorously, the methylene chloride layer is separated, the aqueous layer is further extracted with 200 ml of diethyl ether; the combined extracts are dried (anhydrous magnesium sulfate), decolorized with charcoal, and evaporated to dryness to yield 8,11-dichloro-2-methyl-5H-pyrrolo[2,1-c][1,4]benzodiazepine as a viscous oil which is used in the next step without further purification.

Workup

  1. temperatureThe mixture is heated at 100°-110° for 1 hour
  2. customthe methylene chloride layer is separated
  3. extractionthe aqueous layer is further extracted with 200 ml of diethyl ether
  4. dry with materialthe combined extracts are dried (anhydrous magnesium sulfate)
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-9dbbac41ca5e4330b93825e671a269b4
Source dataset
uspto-grants-1986_06
Patent number
US04596799

Reaction notes

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