Thionyl Chloride → HCID 23317233, compound

HRID 1982105Notes

Reaction equation

HRID 1982105 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:12]([CH3:13])[CH2:11][CH:10](O)[CH2:9][N:8]=[C:7]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:6]=2[CH:21]=1.S(Cl)([Cl:24])=O>C1C=CC=CC=1.C(N(CC)CC)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:12]([CH3:13])[CH:11]([CH2:10][Cl:24])[CH2:9][N:8]=[C:7]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:6]=2[CH:21]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 12318108HCID 12318108, compound

Product 1

HCID 23317233HCID 23317233, compound

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 241BenzeneSolvent

Procedure

A solution of 1 g of 8-chloro-1-methyl-3-hydroxy-6-phenyl-1,2,3,4-tetrahydro-1,5-benzodiazocine in 50 ml benzene was heated under reflux for 1 hour with 1 ml thionylchloride. The solution was reacted with a few drops of triethylamine, washed with water and concentrated by evaporation to dryness in a vacuum. The residue was dissolved in isopropanol and reacted with an ether solution of hydrogen chloride. There was obtained 7-chloro-1-methyl-2-chloromethyl-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepine hydrochloride. The product was also identical with the product obtained in Example 10 of application Ser. No. 335,986; m.p. 110°-112° C.

Workup

  1. washwashed with water
  2. concentrationconcentrated by evaporation to dryness in a vacuum
  3. dissolutionThe residue was dissolved in isopropanol
  4. customreacted with an ether solution of hydrogen chloride

Sources & evidence

ORD record
ord-86de0b4f6d224fd88f0edacaf1fbc5b5
Source dataset
uspto-grants-1986_06
Patent number
US04595531

Reaction notes

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