Water → HCID 66696641, compound

HRID 1672556Notes

Reaction equation

HRID 1672556 reaction equation
[CH2:1]([C:3]1[S:7][C:6]([CH:8]=[O:9])=[CH:5][CH:4]=1)[CH3:2].[N+:10]([CH:12](S(C1C=CC(C)=CC=1)(=O)=O)[CH3:13])#[C-:11].C([O-])([O-])=O.[K+].[K+].O>CO>[CH2:1]([C:3]1[S:7][C:6]([C:8]2[O:9][CH:11]=[N:10][C:12]=2[CH3:13])=[CH:5][CH:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1698305-Ethyl-2-thiophenecarboxaldehydeHCID 110528851-(1-Isocyanoethanesulfonyl)-4-methylbenzene

Product 1

HCID 66696641HCID 66696641, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5-ethylthiophene-2-carbaldehyde (0.670 g, 4.78 mmol), 1-(1-isocyanoethylsulfonyl)-4-methylbenzene (1.0 g, 4.8 mmol), and K2CO3 (0.859 g, 6.21 mmol) in MeOH (16 mL) was heated at reflux for 2 h, then cooled to room temperature and allowed to stand overnight. The mixture was poured into water and extracted with Et2O, and the combined extracts were concentrated in vacuo. The residue was chromatographed on silica gel (Analogix® SF40-115 column, 15% to 30% EtOAc/hexanes eluant, 18 minutes) to afford 0.94 g (102%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 8.26 (s, 1H), 7.15 (d, J=3.6, 1H), 6.91 (dt, J=3.7, 1.0 1H), 2.85 (qd, J=7.5, 0.8 2H), 2.29 (s, 3H), 1.26 (t, J=7.5, 3H). MS (DCI+) m/z 194 (M+H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. extractionextracted with Et2O
  4. concentrationthe combined extracts were concentrated in vacuo
  5. customThe residue was chromatographed on silica gel (Analogix® SF40-115 column, 15% to 30% EtOAc/hexanes eluant, 18 minutes)

Sources & evidence

ORD record
ord-a3be59d50580400b9f66705de58f9c1f
Source dataset
uspto-grants-2011_08
Patent number
US07998993B2

Reaction notes

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