Dimethylformamide → 4-(Thiophen-2-yl)oxane-4-carbonyl chloride

HRID 502957Notes

Reaction equation

HRID 502957 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1([C:12]([OH:14])=O)[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1.S(Cl)([Cl:17])=O.CN(C=O)C>C(Cl)Cl>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1([C:12]([Cl:17])=[O:14])[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 190662544-(Thiophen-2-yl)oxane-4-carboxylic acid

Product 1

HCID 242296654-(Thiophen-2-yl)oxane-4-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(2-Thienyl)tetrahydropyran-4-carboxylic acid was reacted with thionyl chloride and a catalytic amount of DMF in methylene chloride under heating to obtain 4-(2-thienyl)tetrahydropyran-4-carbonyl chloride. A THF solution of 4-(2-thienyl)tetrahydropyran-4-carbonyl chloride was added dropwise to a THF solution of hydrazine monohydrate and the whole was reacted at 0° C. to obtain 4-(2-thienyl)tetrahydropyran-4-carbohydrazide.

Sources & evidence

ORD record
ord-23b80a9997984014b74ec45af4476216
Source dataset
uspto-grants-2010_08
Patent number
US07776897B2

Reaction notes

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