4-Amino-5-chloro-N-(1,2-dimethyl-4-pyrazolidinyl)-2-methoxybenzamide → HCID 13505730, compound

HRID 464400Notes

Reaction equation

[NH2:1][C:2]1[C:17]([Cl:18])=[CH:16][C:5]([C:6]([NH:8][CH:9]2[CH2:13][N:12]([CH3:14])[N:11](C)[CH2:10]2)=[O:7])=[C:4]([O:19][CH3:20])[CH:3]=1.Cl[O-].[Na+]>CO.C(Cl)(Cl)Cl>[NH2:1][C:2]1[C:17]([Cl:18])=[CH:16][C:5]([C:6]([NH:8][CH:9]2[CH2:13][N:12]([CH3:14])[N:11]=[CH:10]2)=[O:7])=[C:4]([O:19][CH3:20])[CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1.44 g (0.00482 mole) of 4-amino-5-chloro-2-methoxy-N-(1,2-dimethyl-4-pyrazolidinyl)benzamide in 100 ml of methanol, cooled to -30° C. and under nitrogen atmosphere was added dropwise 10.5 ml (0.007 mole) of 5% aqueous sodium hypochlorite over a 15 minute period. The mixture was slowly warmed to 0° C. at which temperature it was stirred for 1 hr. The mixture was diluted with 250 ml of chloroform and extracted successively with 100 ml of water and 100 ml of saturated sodium chloride solution. The chloroform layer was dried over sodium sulfate and concentrated in vacuo. The concentrate was filtered through silica gel (eluted with ethyl acetate:hexane:methanol, 4.5:4.5:1). The filtrate was concentrated and the residue was triturated with cold diethyl ether to give 0.58 g (43%) of the title product as white powder, m.p. 173°-175° C.

Workup

extractionextracted successively with 100 ml of water and 100 ml of saturated sodium chloride solution
dry with materialThe chloroform layer was dried over sodium sulfate
concentrationconcentrated in vacuo
filtrationThe concentrate was filtered through silica gel (eluted with ethyl acetate:hexane:methanol, 4.5:4.5:1)
concentrationThe filtrate was concentrated
customthe residue was triturated with cold diethyl ether

Sources & evidence

ORD record: ord-f474cf683c3b4412a22159d5bdaf779e
Source dataset: uspto-grants-1985_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04547518

Reaction notes

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