p-Toluenesulfonic acid monohydrate → HCID 54680218, compound

HRID 845812Notes

Reaction equation

HRID 845812 reaction equation
[OH:1][C:2]1[C:3]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][C:4]=2[S:5][C:6]=1[C:7]([NH2:9])=[O:8].[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)[CH:27]=O)=[CH:22][CH:21]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[OH:1][C:2]1[C:3]2[CH:13]=[C:12]([C:14]([F:17])([F:15])[F:16])[CH:11]=[CH:10][C:4]=2[S:5][C:6]=1[C:7]([NH:9][CH:27]=[C:26]([C:23]1[CH:22]=[CH:21][C:20]([O:19][CH3:18])=[CH:25][CH:24]=1)[C:29]1[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=1)=[O:8]

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 12652957HCID 12652957, compoundHCID 54680210HCID 54680210, compound

Product 1

HCID 54680218HCID 54680218, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3-hydroxy-5-trifluoromethylbenzo[b]thiophene-2-carboxamide (300 mg, 1.15 mmol) in hot toluene (30 ml) were added 2,2-di-(4-methoxyphenyl)acetaldehyde (380 mg, 1.48 mmol) and p-toluenesulfonic acid monohydrate (20 mg). The reaction mixture was stirred at reflux temperature for one hour with azeotropic removal of water, cooled, and evaporated. Trituration of the residue with diethyl ether gave a yellow solid that was filtered, washed with ether, and dried in vacuo; to yield 453 mg (79%) of 3-hydroxy-N-[2,2-di(4-methoxyphenyl)ethenyl]-5-trifluoromethylbenzo[b]-thiophene-2-carboxamide, m.p. 178°-183° C.

Workup

  1. temperatureat reflux temperature for one hour
  2. customwith azeotropic removal of water
  3. temperaturecooled
  4. customevaporated
  5. customTrituration of the residue with diethyl ether gave a yellow solid
  6. filtrationthat was filtered
  7. washwashed with ether
  8. customdried in vacuo

Sources & evidence

ORD record
ord-eb1da8828d4043d3bb217cfd20ea3b7f
Source dataset
uspto-grants-1988_07
Patent number
US04760086

Reaction notes

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