Ethyl chloroformate → Ethyl (2-(thiophen-3-yl)ethyl)carbamate

HRID 2384869Notes

Reaction equation

HRID 2384869 reaction equation
C(N(C(C)C)CC)(C)C.Cl.[S:11]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][NH2:18])=[CH:12]1.Cl[C:20]([O:22][CH2:23][CH3:24])=[O:21]>ClCCl>[CH2:23]([O:22][C:20](=[O:21])[NH:18][CH2:17][CH2:16][C:13]1[CH:14]=[CH:15][S:11][CH:12]=1)[CH3:24]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 122587382-(Thiophen-3-yl)ethan-1-amine hydrochloride

Product 1

HCID 49670241Ethyl (2-(thiophen-3-yl)ethyl)carbamateYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add diisopropylethylamine (54.0 g, 418.0 mmol) to a suspension of 2-thiophene-3-yl-ethylamine hydrochloride in dichloromethane (400 mL) and stir the mixture for 40 min at RT. Cool the mixture to 0° C. and add dropwise ethyl chloroformate (22.7 g, 209.0 mmol) over 15 min. After the addition is complete, stir the reaction for 1 h at 0° C. Wash with 10% sodium bisulfate (500 mL). Extract the aqueous portion with dichloromethane (2×100 mL) and dry the combined organic portions over Na2SO4, filter and concentrate in vacuo. Purify the resulting residue by silica gel chromatography, using an eluent of 100% dichloromethane to give 22.6 g (60%) of the title compound. MS/ES m/z 200.3 [M+H]+.

Workup

  1. temperatureCool the mixture to 0° C.
  2. additionAfter the addition
  3. stirringstir
  4. customthe reaction for 1 h at 0° C
  5. washWash with 10% sodium bisulfate (500 mL)
  6. extractionExtract the aqueous portion with dichloromethane (2×100 mL)
  7. dry with materialdry the combined organic portions over Na2SO4
  8. filtrationfilter
  9. concentrationconcentrate in vacuo
  10. customPurify the resulting residue by silica gel chromatography

Sources & evidence

ORD record
ord-779ac76a520143d8b3320b558aae712d
Source dataset
uspto-grants-2012_09
Patent number
US08263772B2

Reaction notes

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