Hydrochloric Acid → N-(5-Phenyl-2-thienyl)-benzamide

HRID 27665Notes

Reaction equation

HRID 27665 reaction equation
O.O.[I-].[Li+].[Li+].[I-].C(C[C:11]1[CH:15]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[S:13][C:12]=1[NH:22][C:23](=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(O)=O.Cl>N1C(C)=CC(C)=CC=1C.C(Cl)(Cl)Cl.O>[C:16]1([C:14]2[S:13][C:12]([NH:22][C:23](=[O:30])[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[CH:11][CH:15]=2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 66321Lithium iodideHCID 23341625N-(3-Carboxymethyl-5-phenyl-2-thienyl)-benzamideHCID 23688289Lithium iodide (LiI), dihydrate

Product 1

HCID 23341604N-(5-Phenyl-2-thienyl)-benzamideYield 53%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 79532,4,6-TrimethylpyridineSolvent2×

Procedure

Lithium iodide dihydrate (25.5 g, 0.168 mole) in collidine (50 ml) under nitrogen were stirred and refluxed until the LiI dissolved. The amido-ester of Example 52 (17 g, 0.053 mole) in warm collidine (400 ml) was added and the solution stirred and refluxed for 48 hours. The cooled solution was poured into a mixture of 5 N. HCl (800 ml., 4 mole) and ice, extracted with chloroform, which was washed with saturated sodium hydrogen carbonate solution, dried (Na2SO4), and evaporated to leave a semisolid. This was heated in vacuo with water to remove residual collidine, stirred with saturated sodium hydrogen carbonate solution, the solid filtered, washed with water and dried to give the title compound (7.85 g) (m.p. 202°-203° C.).

Workup

  1. dissolutiondissolved
  2. temperaturerefluxed for 48 hours
  3. additionThe cooled solution was poured into a mixture of 5 N
  4. washwas washed with saturated sodium hydrogen carbonate solution
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customto leave a semisolid
  8. customto remove residual collidine
  9. stirringstirred with saturated sodium hydrogen carbonate solution
  10. filtrationthe solid filtered
  11. washwashed with water
  12. customdried

Sources & evidence

ORD record
ord-55d45b2a393f4d35af5f4cb377dc9d25
Source dataset
uspto-grants-1980_09
Patent number
US04222946

Reaction notes

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