Nitrogen mustard hydrochloride → HCID 18180146, compound

HRID 1358940Notes

Reaction equation

HRID 1358940 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:4]=1[NH2:10].[CH3:11][N:12]([CH2:16][CH2:17]Cl)[CH2:13][CH2:14]Cl.Cl.C(=O)([O-])[O-].[K+].[K+]>ClC1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:4]=1[N:10]1[CH2:17][CH2:16][N:12]([CH3:11])[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 5935Nitrogen mustard hydrochlorideHCID 11430Potassium CarbonateHCID 4592492-Methoxy-6-methylaniline

Product 1

HCID 18180146HCID 18180146, compound

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A mixture of 2-methoxy-6-methylphenylamine (D28) (3.62 g, 26.4 mmol), mechlorethamine hydrochloride (12.7 g, 66 mmol) and potassium carbonate (15 g) in chlorobenzene (90 ml) was refluxed under argon for 20 h. The mixture was cooled and filtered, and the filtrate evaporated under reduced pressure to leave the title compound (D29) as a red oil which slowly crystallised on standing (5.4 g, 93%) MH+=221.

Workup

  1. temperaturewas refluxed under argon for 20 h
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-0f5b161a4931434c9baa6af856324eac
Source dataset
uspto-grants-2003_07
Patent number
US06599904B2

Reaction notes

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