Thioglycolic Acid → HCID 131726235, compound

HRID 347448Notes

Reaction equation

HRID 347448 reaction equation
[C:1]([S:14]([N:17]([CH2:19][CH2:20][OH:21])[CH3:18])(=[O:16])=[O:15])([C:4]([C:7]([C:10]([F:13])([F:12])[F:11])([F:9])[F:8])([F:6])[F:5])([F:3])[F:2].[SH:22][CH2:23][C:24](O)=[O:25]>C(S(O)(=O)=O)(F)(F)F.C1(C)C=CC=CC=1>[C:1]([S:14]([N:17]([CH2:19][CH2:20][O:21][C:24]([CH2:23][SH:22])=[O:25])[CH3:18])(=[O:15])=[O:16])([C:4]([C:7]([C:10]([F:11])([F:12])[F:13])([F:9])[F:8])([F:6])[F:5])([F:3])[F:2]

Participants

5

Reactant 2

HCID 1133Thioglycolic AcidHCID 1186882-(N-(Perfluorobutylsulfonyl)-N-methylamino)ethanol

Product 1

HCID 131726235HCID 131726235, compound

Reagents, catalysts & solvents 2

HCID 62406Trifluoromethanesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A 500 mL three-necked round bottom flask was charged with 16.86 g of C4F9SO2N(CH3)CH2CH2OH (MW=357; 47.22 mmol; Example 2, A from WO 01/30873), 4.35 g HSCH2CO2H (MW=92.12, 47.22 mmol; available from Sigma-Aldrich), 2 drops of CF3SO3H catalyst, and 120 mL toluene. The mixture was heated to reflux under nitrogen at 115–120° C. with a mechanical stirrer for 8 hours. Water was removed by azeotropic distillation. Fourier Transform Infrared Spectroscopy (FTIR) analysis indicated the formation of ester. Toluene was stripped using a rotary evaporator (21.35 g solid).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux under nitrogen at 115–120° C. with a mechanical stirrer for 8 hours
  3. customWater was removed by azeotropic distillation
  4. customa rotary evaporator (21.35 g solid)

Sources & evidence

ORD record
ord-6ba264a8b5724a2892a98ad65b286766
Source dataset
uspto-grants-2007_02
Patent number
US07173778B2

Reaction notes

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