Water → HCID 10954430, compound

HRID 989323Notes

Reaction equation

HRID 989323 reaction equation
[NH2:1][C:2]1[C:3]2[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:4]=2[S:5][C:6]=1C(OC)=O.O>CN1CCCC1=O.CN1CCNCC1>[NH2:1][C:2]1[C:3]2[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:4]=2[S:5][CH:6]=1

Participants

5

Reactant 2

HCID 962WaterHCID 2759774methyl 3-amino-5-nitro-1-benzothiophene-2-carboxylate

Product 1

HCID 10954430HCID 10954430, compound

Reagents, catalysts & solvents 2

HCID 13387N-methyl-2-pyrrolidoneSolventHCID 531671-MethylpiperazineSolvent

Procedure

A solution of 23.00 g (91.26 mmol) of methyl 3-amino-5-nitrobenzo[b]thiophene-2-carboxylate (J. Hetero. Chem., 34(4), 1163 (1997)) in 100 mL of 1-methyl-2-pyrrolidinone and 30 mL of 1-methylpiperazine is heated at 180° C. for 2 hours. The reaction is cooled to room temperature and poured into water. The resultant solid is collected by filtration and washed with water. The solid is dissolved in a mixture of ethyl acetate and diethyl ether and the solution is washed with water twice. The organic layer is dried over magnesium sulfate, filtered and concentrated in vacuo. Diethyl ether and hexane are added to the residue and the dark red solid is collected by filtration to provide 11.17 g (63%), mp 155-158° C.

Workup

  1. filtrationThe resultant solid is collected by filtration
  2. washwashed with water
  3. dissolutionThe solid is dissolved in a mixture of ethyl acetate and diethyl ether
  4. washthe solution is washed with water twice
  5. dry with materialThe organic layer is dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. additionDiethyl ether and hexane are added to the residue
  9. filtrationthe dark red solid is collected by filtration
  10. customto provide 11.17 g (63%), mp 155-158° C.

Sources & evidence

ORD record
ord-75bdc5281afb4cb49132c96f25f7e1ae
Source dataset
uspto-grants-2003_10
Patent number
US06638929B2

Reaction notes

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