Dimethylformamide → HCID 57147438, compound

HRID 1086375Notes

Reaction equation

HRID 1086375 reaction equation
[CH2:1]([C:5]1[CH:15]=[CH:14][CH:13]=[CH:12][C:6]=1[CH:7]=[CH:8][C:9](O)=[S:10])[CH2:2][CH2:3][CH3:4].CN(C=O)C.C(Cl)(=O)C([Cl:24])=O>C(Cl)Cl>[CH2:1]([C:5]1[CH:15]=[CH:14][CH:13]=[CH:12][C:6]=1[CH:7]=[CH:8][C:9]([Cl:24])=[S:10])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chloride2×HCID 178440802HCID 178440802, compound

Product 1

HCID 57147438HCID 57147438, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methylene chloride (564 ml) is added to 2-n-butylthiocinnamic acid (40.0 g, 0.69 mol) and cooled in an ice bath. To the mixture is added DMF (13.1 ml, 0.169 mol) and then oxalyl chloride (34.0 ml, 0.389 mol) dropwise with the vigorous evolution of gas. After the oxalyl chloride addition is complete, the ice bath is removed and the reaction stirred at room temperature for 2 hours to afford 2-n-butylthiocinnamic acid chloride. Methylhydroxylamine hydrochloride salt (56.5 g, 0.677 mol) is dissolved in THF (50 ml) and water (70 ml) and further THF (96 ml) is added. The acid chloride is added dropwise then stopped so an additional THF (175 ml) and water (35 ml) can be added for solubility. The acid chloride addition is then continued with the reaction mixture being cooled in an ice bath. After the addition is complete, the reaction mixture is stirred at room temperature overnight.

Workup

  1. temperaturecooled in an ice bath
  2. customthe ice bath is removed

Sources & evidence

ORD record
ord-2374eeb278584a19ab12ddd7bc31d822
Source dataset
uspto-grants-1991_07
Patent number
US05028629

Reaction notes

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