Hydrochloric Acid → HCID 178418672, compound

HRID 5265Notes

Reaction equation

HRID 5265 reaction equation
[CH2:1]1[C:6](=[O:7])[S:5][CH2:4][C:2]1=[O:3].C(N(CC)CC)C.[ClH:15].CN(C)CCCN=C=NCC.Cl[C:28]1[CH:41]=[CH:40][CH:39]=[CH:38][C:29]=1[O:30][CH:31](C)[CH2:32][CH2:33][C:34](O)=O.Cl.CN(C)[CH:45]=[O:46]>CN(C)C1C=CN=CC=1>[OH:3][C:2]1[CH2:4][S:5][C:6](=[O:7])[C:1]=1[C:45](=[O:46])[CH2:34][CH2:33][CH2:32][CH2:31][O:30][C:29]1[CH:28]=[CH:41][C:40]([Cl:15])=[CH:39][CH:38]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10214383Thiotetronic acidHCID 622146894-(Chlorophenoxy]pentanoic acid

Product 1

HCID 178418672HCID 178418672, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a stirring solution of 224 mg (1.89 mmol) of thiotetronic acid in 10 mL of dimethylformamide is added 290 μL (2.08 mmol) of triethylamine and 77 mg (631 μmol) of 4-dimethylaminopyridine at 0° C. Next, 440 mg (2.29 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 530 mg (2.32 mmol) of 5-[4-(chlorophenoxy]pentanoic acid are added and the reaction mixture is stirred overnight at room temperature. The reaction is acidified with 1.0N HCl and extracted three times with ether. The combined organic layers are dried over Na2SO4 and concentrated in vacuo giving a yellow solid. The residue is recrystallized from ethyl acetate/hexane at -78° C. to give 150 mg (24%) of 4-hydroxy-3-[5-(4-chlorophenoxy)-1-oxopentyl]-2(5H)-thiophenone.

Workup

  1. extractionextracted three times with ether
  2. dry with materialThe combined organic layers are dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customgiving a yellow solid
  5. customThe residue is recrystallized from ethyl acetate/hexane at -78° C.

Sources & evidence

ORD record
ord-3d699815cf194d7584f2790f886973cf
Source dataset
uspto-grants-1993_09
Patent number
US05242945

Reaction notes

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