p-Toluenesulfonic acid → HCID 90418372, compound

HRID 2177364Notes

Reaction equation

HRID 2177364 reaction equation
[NH2:1][C:2]1[S:3][CH:4]([CH3:17])[C:5](O)([C:12]([F:15])([F:14])[F:13])[C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].CC1C=CC(S(O)(=O)=O)=CC=1>ClCCl>[NH2:1][C:2]1[S:3][C:4]([CH3:17])=[C:5]([C:12]([F:14])([F:13])[F:15])[C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 90418142HCID 90418142, compound

Product 1

HCID 90418372HCID 90418372, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

Into a 100-mL round-bottom flask, was placed ethyl 2-amino-4-hydroxy-5-methyl-4-(trifluoromethyl)-4,5-dihydrothiophene-3-carboxylate (5.7 g, 21.01 mmol, 1.00 equiv), dichloromethane (20 mL), 4-methylbenzene-1-sulfonic acid (3.6 g, 20.91 mmol, 0.99 equiv). The resulting solution was stirred overnight at 25° C. The solids were filtered out. The filtrate was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (40/60). The collected fractions were combined and concentrated under vacuum. This resulted in 3.95 g (71%) of ethyl 2-amino-5-methyl-4-(trifluoromethyl)thiophene-3-carboxylate as yellow oil.

Workup

  1. customInto a 100-mL round-bottom flask, was placed
  2. filtrationThe solids were filtered out
  3. concentrationThe filtrate was concentrated under vacuum
  4. concentrationconcentrated under vacuum
  5. customThis resulted in 3.95 g (71%) of ethyl 2-amino-5-methyl-4-(trifluoromethyl)thiophene-3-carboxylate as yellow oil

Sources & evidence

ORD record
ord-3701400bb600491ea3d5a297d1ab4eb0
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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