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

HRID 1448709
Notes
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Reaction equation

HRID 1448709 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 962
Water
Solvent
HCID 6212ChloroformSolvent
HCID 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 5N. 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 5N
  4. washwas washed with saturated sodium hydrogen carbonate solution
  5. customdried (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-e15e4d2a9d9d447ca63c42ebbd0e85a4
Source dataset
uspto-grants-1980_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04187232

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes