Toluene → HCID 16110263, compound

HRID 2224613Notes

Reaction equation

HRID 2224613 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-913ff37012264a3391772f02fc98f49a
Source dataset
uspto-grants-2008_05
Patent number
US07378431B2

Reaction notes

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