Sodium methanesulfinate → HCID 90418475, compound

HRID 2177236Notes

Reaction equation

HRID 2177236 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:12](I)[S:11][N:10]=2)=[CH:5][CH:4]=1)[CH3:2].[CH3:20][S:21]([O-:23])=[O:22].[Na+]>[Cu]I.CN(C)C=O>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:12]([S:21]([CH3:20])(=[O:23])=[O:22])[S:11][N:10]=2)=[CH:5][CH:4]=1)[CH3:2]

Participants

5

Reactant 2

HCID 2733271Sodium methanesulfinateHCID 90418750HCID 90418750, compound

Product 1

HCID 90418475HCID 90418475, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Into a 50-mL round-bottom flask, was placed N,N-dimethylformamide (8 mL), CuI (391 mg, 2.05 mmol, 1.99 equiv), ethyl 3-(4-ethylphenyl)-5-iodo-1,2-thiazole-4-carboxylate (400 mg, 1.03 mmol, 1.00 equiv), sodium methanesulfinate (421.7 mg, 4.13 mmol, 4.00 equiv). The resulting solution was stirred for 16 h at 80° C. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:20). The collected fractions were combined and concentrated under vacuum. This resulted in 170 mg (48%) of ethyl 3-(4-ethylphenyl)-5-methanesulfonyl-1,2-thiazole-4-carboxylate as a yellow solid. Mass spectrum (ESI, m/z): Calcd. for C15H17NO4S2, 340.1 (M+H). found 340.1.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. concentrationconcentrated under vacuum
  4. customThis resulted in 170 mg (48%) of ethyl 3-(4-ethylphenyl)-5-methanesulfonyl-1,2-thiazole-4-carboxylate as a yellow solid

Sources & evidence

ORD record
ord-3e81f30873d24f18b0a50f2fff48dcd4
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

Loading…