Water → Methyl 3-[4-(sec-butyl)phenylsulfonamido]thiophene-2-carboxylate

HRID 1925702Notes

Reaction equation

HRID 1925702 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([O:9][CH3:10])=[O:8].N1C=CC=CC=1.[CH:17]([C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1)([CH2:19][CH3:20])[CH3:18].O>ClCCl>[CH:17]([C:21]1[CH:26]=[CH:25][C:24]([S:27]([NH:1][C:2]2[CH:6]=[CH:5][S:4][C:3]=2[C:7]([O:9][CH3:10])=[O:8])(=[O:29])=[O:28])=[CH:23][CH:22]=1)([CH2:19][CH3:20])[CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 89652Methyl 3-amino-2-thiophenecarboxylateHCID 37760484-(Butan-2-yl)benzene-1-sulfonyl chloride

Product 1

HCID 19683026Methyl 3-[4-(sec-butyl)phenylsulfonamido]thiophene-2-carboxylateYield 49.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of methyl 3-aminothiophene-2-carboxylate (0.68 g; 4.3 mmol) in pyridine (0.52 mL; 6.4 mmol) and anhydrous dichloromethane (15 mL), was added a solution of 51 (1.0 g; 4.3 mmol) in dichloromethane (3 mL). After stirring 16 hours at room temperature, the reaction was mixed with water (50 mL), and the organic phase was separated. The aqueous phase was extracted with dichloromethane (2×10 mL), and the combined organic phases were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel eluting with ethyl acetate/hexanes (0 to 25% v/v gradient elution) to yield the title product as a white solid (0.75 g).

Workup

  1. customthe organic phase was separated
  2. extractionThe aqueous phase was extracted with dichloromethane (2×10 mL)
  3. dry with materialthe combined organic phases were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude residue was purified by flash chromatography on silica gel eluting with ethyl acetate/hexanes (0 to 25% v/v gradient elution)

Sources & evidence

ORD record
ord-ceee2b64039541bfaf48810e54d7574c
Source dataset
uspto-grants-2012_05
Patent number
US08178699B2

Reaction notes

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