Dimethyl oxalate → HCID 21388392, compound

HRID 1834039Notes

Reaction equation

HRID 1834039 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C:11]([O:17][CH3:18])(=[O:16])[C:12](OC)=[O:13]>>[C:4]([C:3]1[CH:6]=[CH:7][C:8]([NH:10][C:12](=[O:13])[C:11]([O:17][CH3:18])=[O:16])=[CH:9][C:2]=1[NH:1][C:12](=[O:13])[C:11]([O:17][CH3:18])=[O:16])#[N:5]

Participants

3

Reactant 2

HCID 11120Dimethyl oxalateHCID 132271905-Amino-2-fluorobenzonitrile

Product 1

HCID 21388392HCID 21388392, compoundYield 81%

Procedure

A mixture of 29.0 grams (0.218 mole) of 2,4-diaminobenzonitrile and 255 grams of dimethyl oxalate is refluxed for 3 hours. The excess dimethyl oxalate is distilled off in vacuo. The residue is boiled with 150 ml. of methanol and filtered. The filtrate is poured into 900 ml. of water and the tan precipitate removed by filtration. There is obtained 53.7 grams (81%) of tan needles melting at 155°-160°. The product is boiled in 1800 ml. of methanol and the insoluble material removed by filtration. The filtrate is poured into 2 liters of water, refrigerated, and the precipitate removed by filtration. There is obtained 23.8 grams of fine yellow needles melting at 160°-163°.

Workup

  1. temperatureis refluxed for 3 hours
  2. distillationThe excess dimethyl oxalate is distilled off in vacuo
  3. filtrationof methanol and filtered
  4. additionThe filtrate is poured into 900 ml
  5. customof water and the tan precipitate removed by filtration

Sources & evidence

ORD record
ord-0ceb263e68d54c92a17e901fe82e5d4d
Source dataset
uspto-grants-1978_01
Patent number
US04067995

Reaction notes

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