Dimethylformamide → HCID 22222887, compound

HRID 979635Notes

Reaction equation

HRID 979635 reaction equation
Cl.[NH2:2][OH:3].[C:4](=[O:7])([O-])[O-].[Na+].[Na+].[CH3:10][O:11][C:12]([C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Br)=[CH:16][CH:15]=1)=[O:13].CN(C)[CH:24]=[O:25]>>[CH3:10][O:11][C:12]([C:14]1[CH:21]=[CH:20][C:17]([CH2:18][N:2]([CH2:12][C:14]2[CH:21]=[CH:20][C:17]([C:4]([O:25][CH3:24])=[O:7])=[CH:16][CH:15]=2)[OH:3])=[CH:16][CH:15]=1)=[O:13]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 10340Sodium CarbonateHCID 256687Methyl 4-(bromomethyl)benzoateHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 22222887HCID 22222887, compound

Procedure

To a stirred suspension of 1.11 grams of hydroxylamine hydrochloride and 6.78 grams of anhydrous sodium carbonate in 20 ml of dry N,N-dimethylformamide (DMF) is added a solution of 7.49 grams of p-methoxycarbonylbenzyl bromide in 30 ml of dry DMF. The mixture is stirred at ambient temperature for 24 hours. Insoluble material present is removed by filtration and the filtrate is concentrated. The above-named product is obtained from the resulting residue by preparative liquid chromatography as 2.8 grams of a white solid, melting at 129°-131° C.

Workup

  1. customInsoluble material present is removed by filtration
  2. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-f706b8a7c8f24ebea7d77960e4946bfe
Source dataset
uspto-grants-1987_05
Patent number
US04668727

Reaction notes

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