Bromoform → (2Z)-2-[2-(benzhydryloxyamino)-2-oxoethoxy]imino-2-(furan-2-yl)acetic acid

HRID 851556Notes

Reaction equation

HRID 851556 reaction equation
Cl[CH2:2][C:3]([NH:5][O:6][CH:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4].[O:20]1[CH:24]=[CH:23][CH:22]=[C:21]1/[C:25](=[N:29]/[OH:30])/[C:26]([OH:28])=[O:27].C(Cl)(Cl)(Cl)Cl.ClCCl.C(Br)(Br)Br>CS(C)=O.CCO>[C:8]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:6][NH:5][C:3]([CH2:2][O:30]/[N:29]=[C:25](/[C:21]2[O:20][CH:24]=[CH:23][CH:22]=2)\[C:26]([OH:28])=[O:27])=[O:4])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 5558BromoformHCID 12774346Diphenylmethyl ChloroacetohydroxamateHCID 14556124HCID 14556124, compoundHCID 22996148Carbon tetrachloride methylene chloride

Product 1

HCID 88738326(2Z)-2-[2-(benzhydryloxyamino)-2-oxoethoxy]imino-2-(furan-2-yl)acetic acidYield 17%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Procedure

This was prepared from diphenylmethyl chloroacetohydroxamate and Z-2-(fur-2-yl)-2-hydroxyiminoacetic acid by the method described in Preparation 4; m.p. 138°-140° (from carbon tetrachloride-dichloromethane), λmax (EtOH) 273.5 nm (ε13,900), νmax (CHBr3) 3350 (NH), ca 3600-2100 (bonded OH), 1750 and 1728 (CO2H), 1690 cm-1 (CONH), τ(DMSO d6) include 2.09, 3.20 and 3.30 (α-furyl), 2.4-2.8 (Ph), 4.00 (Ph2CH), 5 49 (CH2). Yield 17%.

Workup

  1. customdescribed in Preparation 4

Sources & evidence

ORD record
ord-e849ec5181f84cd2a9fb557ea3f0480d
Source dataset
uspto-grants-1983_05
Patent number
US04385177

Reaction notes

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