Pyridine → Ethyl 3-methyl-5-(phenoxycarbonylamino)thiophene-2-carboxylate

HRID 560555Notes

Reaction equation

HRID 560555 reaction equation
[NH2:1][C:2]1[S:6][C:5]([C:7]([O-:9])=[O:8])=[C:4]([CH3:10])[CH:3]=1.N1C=CC=[CH:13][CH:12]=1.Cl[C:18]([O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19]>ClCCl>[CH3:10][C:4]1[CH:3]=[C:2]([NH:1][C:18]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:19])[S:6][C:5]=1[C:7]([O:9][CH2:12][CH3:13])=[O:8]

Participants

5

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 866452885-Amino-3-methylthiophene-2-carboxylate

Product 1

HCID 43403943Ethyl 3-methyl-5-(phenoxycarbonylamino)thiophene-2-carboxylateYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 5-amino-3-methylthiophene-2-carboxylate (11.87 g, 64.08 mmol) and pyridine (5.70 mL, 70.48 mml) in dichloromethane (140 mL) at 0° C. was added dropwise phenyl chloroformate (8.90 mL, 70.71 mmol). The resulting reaction mixture was stirred at ambient temperature for 30 minutes, and then quenched with water (200 mL). The aqueous layer was extracted with dichloromethane (2×200 mL), and the combined organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was triturated with dichloromethane in hexanes to afford ethyl 3-methyl-5-(phenoxycarbonylamino)thiophene-2-carboxylate as a colorless solid (18.89 g, 96%): MS (ES+) m/z 306.1 (M+1).

Workup

  1. customThe resulting reaction mixture
  2. customquenched with water (200 mL)
  3. extractionThe aqueous layer was extracted with dichloromethane (2×200 mL)
  4. dry with materialthe combined organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with dichloromethane in hexanes

Sources & evidence

ORD record
ord-6df8a461fd9749b2acf2f8a0b5939cae
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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