Thionyl Chloride → HCID 19351082, compound

HRID 1636382Notes

Reaction equation

HRID 1636382 reaction equation
[CH2:1]([N:3]([CH2:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([CH2:17][NH:18][NH:19][C:20]([C:22]1[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][CH:23]=1)=[O:21])[CH:11]=[CH:10]2)[CH2:4][CH3:5])[CH3:2].S(Cl)([Cl:33])=O>CN(C)C=O.C(OCC)C>[CH2:1]([N:3]([CH2:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([CH2:17][NH:18][NH:19][C:20]([C:22]1[CH:30]=[CH:29][C:25]([C:26]([Cl:33])=[O:27])=[CH:24][CH:23]=1)=[O:21])[CH:11]=[CH:10]2)[CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 19351179HCID 19351179, compound

Product 1

HCID 19351082HCID 19351082, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-[6-(diethylaminomethyl)naphth-2-ylmethylaminocarbamoyl]benzoic acid (3.1 g, 7.6 mmol) and thionyl chloride (1.1 ml, 15.2 mmol) in dimethylformamide (30 ml) was stirred overnight at room temperature, then the suspension was diluted with diethyl ether and the solid was filtered and dried yielding 3.2 g of crude 4-[6-(diethylaminomethyl)naphth-2-ylmethylaminocarbamoyl]benzoyl chloride. This compound was added as solid to a solution of hydroxylamine hydrochloride (0.6 g, 8.5 mmol) and sodium bicarbonate (1.2 g, 14 mmol) and 1N sodium hydroxide (8.5 ml, 8.5 mmol) in water (30 ml) and THF (40 ml). The mixture was stirred at room temperature for 2 hours, then the mixture was saturated with sodium chloride and the organic phase was separated and the aqueous phase was extracted with THF. The combined organic phases were dried foyer anhydrous sodium sulphate and the solvent was removed under reduced pressure. Crude was dissolved in hot THF (150 ml) and the insoluble material was filtered off. The solution was cooled at room temperature and treated with 1.5 N etheric solution of HCl. The solid product was filtered and dried yielding 1.2 g (yield 38%) of pure 4-[6-(diethylaminomethyl)naphth-2-ylmethylaminocarbamoyl]-benzohydroxamic acid hydrochloride as white solid; m.p.=167-168° C. (dec.)

Workup

  1. filtrationthe solid was filtered
  2. customdried

Sources & evidence

ORD record
ord-dfb984a4fe1d4d20a8fc73151f253dbb
Source dataset
uspto-grants-2000_03
Patent number
US06034096

Reaction notes

Loading…