Aniline → 4-Hydroxy-1,1-dioxo-N-phenyl-1,2-dihydro-1-benzothiopyran-3-carboxamide

HRID 597261Notes

Reaction equation

HRID 597261 reaction equation
[OH:1][C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5](=[O:13])(=[O:12])[CH2:4][C:3]=1[C:14]([O:16]C)=O.[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1(C)C(C)=CC=CC=1>[OH:1][C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5](=[O:12])(=[O:13])[CH2:4][C:3]=1[C:14]([NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16]

Participants

4

Reactant 2

HCID 6115AnilineHCID 54715743HCID 54715743, compound

Product 1

HCID 706325224-Hydroxy-1,1-dioxo-N-phenyl-1,2-dihydro-1-benzothiopyran-3-carboxamide

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Preparation by Aminolysis of the β-Ketoester. -- A mixture of 11.7 g. (0.05 mole) of methyl 4-hydroxy-2H-1-benzothiopyran-3-carboxylate 1,1-dioxide, 7.0 g. (0.075 mole) of aniline, and 250 ml. of xylene was refluxed for 16 hr. in a Soxhlet apparatus, the thimble of which contained 20 g. of Linde type 4A molecular sieve. The mixture was cooled and the resulting precipitate was collected to give 12.8 g. (81%) of product, m.p. 204°-208° dec. Recrystallization from ethyl acetate gave 11.4 g. material, m.p. 205°-208° dec.

Workup

  1. addition-- A mixture of 11.7 g
  2. temperatureThe mixture was cooled
  3. customthe resulting precipitate was collected
  4. customto give 12.8 g
  5. customRecrystallization from ethyl acetate
  6. customgave 11.4 g

Sources & evidence

ORD record
ord-20a9e7cf00964a2e8f21091819ae5288
Source dataset
uspto-grants-1977_03
Patent number
US04013686

Reaction notes

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