Methane → HCID 131712839, compound

HRID 1702847

Reaction equation

HRID 1702847 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([Cl:16])=[N:8][C:9]2[C:14]([N:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:5])[CH3:2].C.[CH2:18]([NH:22][C:23]([NH:25][CH2:26][CH2:27][CH2:28][CH3:29])=[S:24])[CH2:19][CH2:20][CH3:21]>CC(C)=O>[ClH:16].[CH2:1]([O:3][C:4]([C:6]1[C:7]([S:24][C:23]([NH:25][CH2:26][CH2:27][CH2:28][CH3:29])=[N:22][CH2:18][CH2:19][CH2:20][CH3:21])=[N:8][C:9]2[C:14]([N:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 297Methane2×HCID 2723622N,N'-DibutylthioureaHCID 12283436Ethyl 3-Chloroquinoxaline-2-carboxylate

Product 1

HCID 131712839HCID 131712839, compoundYield 47.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

2-Chloro-3-quinoxalinecarboxylic acid ethyl ester (7.10 g., 0.03 mole) was dissolved in 125 ml. of acetone treated with Norit and filtered. The filtrate was added to 5.650 g. (0.03 mole) of 1,3-di-n-butylthiourea in 100 ml. of acetone. The solution was stirred at reflux under a nitrogen atmosphere for 6 hours, allowed to cool to room temperature, and stirred an additional 17 hours. The red solution was treated with Norit, filtered, and concentrated to a volume of 100 ml. The yellow solid that crystallized out was collected by filtration, washed and dried to give the 6.05 g. (47.5% yield) of product, m.p. 138°-139° C. (dec.).

Workup

  1. filtrationfiltered
  2. additionThe filtrate was added to 5.650 g
  3. temperatureat reflux under a nitrogen atmosphere for 6 hours
  4. stirringstirred an additional 17 hours
  5. filtrationfiltered
  6. concentrationconcentrated to a volume of 100 ml
  7. customThe yellow solid that crystallized out
  8. filtrationwas collected by filtration
  9. washwashed
  10. customdried
  11. customto give the 6.05 g

Sources & evidence

ORD record
ord-f825206e528846759b677540039b12f1
Source dataset
uspto-grants-1982_09
Patent number
US04349674

Linked notes

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