HCID 13519238, compound → HCID 13519245, compound

HRID 1980552Notes

Reaction equation

C(OC(=O)C(N=NC1C=CC=CC=1N(C1C=CC=C(C(F)(F)F)C=1)C(OCC)=O)(NC(=O)CCl)C(OCC)=O)C.C(OC(=O)[C:45]([N:56]=[N:57][C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][C:59]=1[N:64]([C:70]1[CH:75]=[CH:74][CH:73]=[C:72]([CH3:76])[C:71]=1[CH3:77])[C:65]([O:67][CH2:68][CH3:69])=[O:66])([NH:51][C:52](=O)[CH2:53][Cl:54])[C:46]([O:48]CC)=[O:47])C>>[CH2:68]([O:67][C:65]([N:64]([C:70]1[CH:75]=[CH:74][CH:73]=[C:72]([CH3:76])[C:71]=1[CH3:77])[C:59]1[CH:60]=[CH:61][CH:62]=[CH:63][C:58]=1[N:57]1[C:52]([CH2:53][Cl:54])=[N:51][C:45]([C:46]([OH:48])=[O:47])=[N:56]1)=[O:66])[CH3:69]

Participants

Reactant 2

HCID 13519238HCID 13519238, compound

HCID 13519239HCID 13519239, compound

Product 1

HCID 13519245HCID 13519245, compound

Procedure

using 98.50 g (0.168 mol) of [2-(N-ethoxycarbonyl-3-(trifluoromethyl)-phenylamino)-phenylazo]-(2-chloroacetamido)-malonic acid diethyl ester there is obtained crude 1-[2-[N-ethoxycarbonyl-3-(trifluoromethyl)-phenylamino]-phenyl]-5-(chloromethyl)-1H-1,2,4-triazole-3-carboxylic acid which sinters from 88° and melts at 100°-108° with decomposition; using 91.10 g (0.166 mol) of [2-(N-ethoxycarbonyl-2,3-dimethylphenylamino)-phenylazo]-(2-chloroacetamido)-malonic acid diethyl ester there is obtained crude 1-[2-(N-ethoxycarbonyl-2,3-dimethylphenylamino)-phenyl]-5-(chloromethyl)-1H-1,2,4-triazole-3-carboxylic acid which melts at 188°-190° with decomposition;

Workup

customthere is obtained crude 1-[2-[N-ethoxycarbonyl-3-(trifluoromethyl)-phenylamino]-phenyl]-5-(chloromethyl)-1H-1,2,4-triazole-3-carboxylic acid which
customsinters from 88°

Sources & evidence

ORD record: ord-306f8257f64f4e8aa63244dbad1276ce
Source dataset: uspto-grants-1985_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04510141

Reaction notes

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