Phosphorus oxychloride → HCID 12318099, compound

HRID 1389028Notes

Reaction equation

HRID 1389028 reaction equation
[CH3:1][N:2]([CH2:10][CH:11](O)[CH2:12][NH:13][C:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][CH:4]=1.P(Cl)(Cl)([Cl:25])=O>[N+](C1C=CC=CC=1)([O-])=O>[ClH:9].[Cl:25][CH:11]1[CH2:12][N:13]=[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:4]2[CH:5]=[C:6]([Cl:9])[CH:7]=[CH:8][C:3]=2[N:2]([CH3:1])[CH2:10]1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 12318087HCID 12318087, compound

Product 1

HCID 12318099HCID 12318099, compound

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 32 grams of N-methyl-N-(2-hydroxy-3-benzoylaminopropyl)-4-chloroaniline and 50 milliliters of phosphorus oxychloride and 100 milliliters of nitrobenzene was heated at a temperature of 95° C. during the course of 22 hours. The excess phosphorus oxychloride and the nitrobenzene were then distilled therefrom at a subatmospheric pressure. The residue was then extracted with chloroform and treated with ice water and dilute sodium hydroxide as described hereinbefore in Example 1. The chloroform extract was then concentrated by evaporation at a subatmospheric pressure. The residue was dissolved in diethyl ether and an isopropanol solution of hydrogen chloride was then added thereto. After recrystallization from a mixture of ethanol and diethyl ether there was obtained 3,8-dichloro-1-methyl-6-phenyl-1,2,3,4-tetrahydro-1,5-benzodiazocine hydrochloride having a melting point of 195°-196° C.

Workup

  1. distillationThe excess phosphorus oxychloride and the nitrobenzene were then distilled
  2. extractionThe residue was then extracted with chloroform
  3. additiontreated with ice water and dilute sodium hydroxide
  4. extractionThe chloroform extract
  5. concentrationwas then concentrated by evaporation at a subatmospheric pressure
  6. dissolutionThe residue was dissolved in diethyl ether
  7. additionan isopropanol solution of hydrogen chloride was then added
  8. customAfter recrystallization
  9. additionfrom a mixture of ethanol

Sources & evidence

ORD record
ord-9e538bc9c35c4211b814e84a3b31aca5
Source dataset
uspto-grants-1981_01
Patent number
US04243585

Reaction notes

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