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

HRID 2067328Notes

Reaction equation

HRID 2067328 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-45dfca6124df433cb0ccb9fa9460a106
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

Loading…