Aniline → HCID 22751984, compound

HRID 372743Notes

Reaction equation

HRID 372743 reaction equation
[O:1]=[C:2]1[CH:7]([C:8]([O:10]C)=O)[CH2:6][S:5][C:4]2[S:12][CH:13]=[CH:14][C:3]1=2.[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1(C)C(C)=CC=CC=1>[O:1]=[C:2]1[CH:7]([C:8]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:10])[CH2:6][S:5][C:4]2[S:12][CH:13]=[CH:14][C:3]1=2

Participants

4

Reactant 2

HCID 6115AnilineHCID 21318614HCID 21318614, compound

Product 1

HCID 22751984HCID 22751984, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of methyl 5,6-dihydro-4-oxo-4H-thieno[2,3-b]-thiopyran-5-carboxylate (5.7 g, 0.025 mole), aniline (3.5 g, 0.0375 mole) and xylene (180 ml) is refluxed for 2.5 hrs. in a Soxhlet apparatus, the thimble of which contains 20 g of Linde type 4A molecular sieve. The mixture is cooled in an ice bath, and the resulting crystalline precipitate (m.p. 155°-158° C.) is collected, dried and recrystallized from methylene chloride and isopropyl ether to give 6.5 g (90%) of off-white crystalline material, m.p. 155°-158° C.

Workup

  1. temperatureis refluxed for 2.5 hrs
  2. temperatureThe mixture is cooled in an ice bath
  3. customthe resulting crystalline precipitate (m.p. 155°-158° C.) is collected
  4. customdried
  5. customrecrystallized from methylene chloride and isopropyl ether

Sources & evidence

ORD record
ord-d82ef64c1b874f399097a122940ab86c
Source dataset
uspto-grants-1978_05
Patent number
US04092325

Reaction notes

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