Toluene → HCID 16110263, compound

HRID 902149Notes

Reaction equation

HRID 902149 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%

Procedure

To a suspension of 44.0 g (164 mmol) of N-(4-methoxy-2-nitrophenyl)-oxalamic acid ethyl ester [J. Med. Chem., 18, 926 (1975)] in 330 ml of toluene 16.8 ml (170 mmol) of n-butylamine is added dropwise keeping the temperature below 20° C., then the mixture is stirred at room temperature overnight. The reaction mixture is concentrated and 200 ml of diethyl ether is added to the residue. The so obtained suspension is filtered, washed with diethyl ether and dried to yield 45.3 g (93%) of the title compound. Mp.: 127-128° C. (diethyl ether).

Workup

  1. additionis added dropwise
  2. customthe temperature below 20° C.
  3. concentrationThe reaction mixture is concentrated
  4. addition200 ml of diethyl ether is added to the residue
  5. customThe so obtained suspension
  6. filtrationis filtered
  7. washwashed with diethyl ether
  8. customdried

Sources & evidence

ORD record
ord-bc46601abbce42ba82bc4ecebe0aa407
Source dataset
uspto-grants-2008_04
Patent number
US07365083B2

Reaction notes

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