Toluene → HCID 16110263, compound

HRID 896439Notes

Reaction equation

HRID 896439 reaction equation
C(O[C:4](=[O:19])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=1[N+:16]([O-:18])=[O:17])=[O:6])C.C1(C)C=CC=CC=1.[CH2:27]([NH2:31])[CH2:28][CH2:29][CH3:30]>>[CH2:27]([NH:31][C:4](=[O:19])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=1[N+:16]([O-:18])=[O:17])=[O:6])[CH2:28][CH2:29][CH3:30]

Participants

4

Reactant 3

HCID 1140TolueneHCID 8007ButylamineHCID 2880788HCID 2880788, compound

Product 1

HCID 16110263HCID 16110263, compoundYield 93.3%

Procedure

To a suspension of 44.0 g (164 mmol) of N-(4-methoxy-2-nitro-phenyl)oxalamic acid ethyl ester [J. Med. Chem., 18, 926 (1975)] and 330 ml toluene 16.8 ml (170 mmol) of n-butylamin is added under 20° C. The reaction mixture is stirred at room temperature for 10 h, then concentrated and the residue is crystallized with diethyl ether, the precipitated product is filtered off, washed with diethyl ether and dried to yield 45.3 g (93.3%) of the title compound. Mp.: 127-128° C. (diethyl ether).

Workup

  1. additionis added under 20° C
  2. concentrationconcentrated
  3. customthe residue is crystallized with diethyl ether
  4. filtrationthe precipitated product is filtered off
  5. washwashed with diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-bfa509d97aea4820a33d6d02f2ac9e9d
Source dataset
uspto-grants-2005_07
Patent number
US06919355B2

Reaction notes

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