Carbon Dioxide → HCID 70598027, compound

HRID 1388201Notes

Reaction equation

HRID 1388201 reaction equation
[CH2:1]([C:3]1[CH:7]=[CH:6][S:5][C:4]=1[CH3:8])[CH3:2].CC1SC=CC=1.P(Cl)(Cl)(Cl)(Cl)Cl.ClS(O)(=O)=O.C(N)(C)(C)C.C([Li])CCC.[C:36](=[O:38])=[O:37].CC1SC([S:45](=[O:52])(=[O:51])[NH:46][C:47]([CH3:50])([CH3:49])[CH3:48])=C(C(O)=O)C=1>>[CH2:1]([C:3]1[C:7]([C:36]([OH:38])=[O:37])=[C:6]([S:45](=[O:52])(=[O:51])[NH:46][C:47]([CH3:50])([CH3:49])[CH3:48])[S:5][C:4]=1[CH3:8])[CH3:2]

Participants

9

Reactant 8

HCID 280Carbon DioxideHCID 6385Tert-ButylamineHCID 111262-MethylthiopheneHCID 24638Chlorosulfonic acid2×HCID 24819Phosphorus pentachlorideHCID 64271113-Ethyl-2-methylthiopheneHCID 23331879HCID 23331879, compoundHCID 178418339Butyllithium

Product 1

HCID 70598027HCID 70598027, compound

Procedure

3-ethyl-2-methyl-thiophene [W. Steinkopf, A. Merckoll and H. Straunch, Liebigs Ann. Chem. 545,45 (1940)] was reacted, analogous to 2-methyl-thiophene (see Example 5) with phosphorus pentachloride and chlorosulfonic acid, and the resulting sulfochloride was treated with tert. butylamine. By metalizing with n-butyl-lithium and carboxylating with carbon dioxide, also in analogy to the preparation of 5-methyl-2-(N-tert. butyl) sulfamoyl-thiophene-3-carboxylic acid, 4-ethyl-5-methyl-2-(N-tert. butyl) sulfamoyl-thiophene-3-carboxylic acid was obtained. Rf -value: 0.27 (TLC-prefabricated plates, silica gel 60 F254, thickness of the layer 0.25 mm, eluant:ethylene chloride/ethyl acetate/glacial acetic acid 100:30:5);

Sources & evidence

ORD record
ord-9b4e6daf445d44f9b1660d14970d70b6
Source dataset
uspto-grants-1984_02
Patent number
US04430355

Reaction notes

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