Nitrogen mustard hydrochloride → HCID 19066167, compound

HRID 481357Notes

Reaction equation

HRID 481357 reaction equation
[NH2:1][C:2]1[C:3]([OH:12])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.Cl.Cl[CH2:15][CH2:16][N:17]([CH2:19][CH2:20]Cl)[CH3:18].C(=O)([O-])[O-].[Na+].[Na+]>C(O)CCC>[CH3:18][N:17]1[CH2:19][CH2:20][N:1]([C:2]2[C:3]([OH:12])=[CH:4][C:5]3[C:10]([CH:11]=2)=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 5935Nitrogen mustard hydrochlorideHCID 10340Sodium CarbonateHCID 794493-Amino-2-naphthol

Product 1

HCID 19066167HCID 19066167, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

3-Aminonaphthalen-2-ol (5 g, 31.4 mmol) is brought to the reflux point of 1-butanol (100 ml) in the presence of 2-chloro-N-(chloroethyl)-N-methylethanamine hydrochloride (6.05 g, 31.4 mmol) and sodium carbonate (1.7 g, 16 mmol). After 48 h, the reaction mixture is concentrated and impregnated onto silica and then purified by flash chromatography with a mixture (93/7/1) of dichloromethane/methanol/aqueous ammonia.

Workup

  1. concentrationthe reaction mixture is concentrated
  2. custompurified by flash chromatography with a mixture (93/7/1) of dichloromethane/methanol/aqueous ammonia

Sources & evidence

ORD record
ord-49feadd111864839b15174d670d3ef17
Source dataset
uspto-grants-1998_08
Patent number
US05789412

Reaction notes

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