Methyl chloroformate → N-cyclopropyl-2-[3-(3-thienyl)phenoxy]ethoxyacetamide

HRID 1756168Notes

Reaction equation

HRID 1756168 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]([CH:17]=[CH:18][CH:19]=2)[O:9][CH2:10][CH2:11][O:12][CH2:13][C:14]([OH:16])=O)=[CH:2]1.ClC(OC)=O.C(N(CC)CC)C.[CH:32]1([NH2:35])[CH2:34][CH2:33]1>O1CCCC1.O.C(OCC)C>[CH:32]1([NH:35][C:14](=[O:16])[CH2:13][O:12][CH2:11][CH2:10][O:9][C:8]2[CH:17]=[CH:18][CH:19]=[C:6]([C:3]3[CH:4]=[CH:5][S:1][CH:2]=3)[CH:7]=2)[CH2:34][CH2:33]1

Participants

8

Reactant 4

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 69828CyclopropylamineHCID 199171292-[3-(3-Thienyl)phenoxy]ethoxyacetic acid

Product 1

HCID 19917094N-cyclopropyl-2-[3-(3-thienyl)phenoxy]ethoxyacetamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.36 g of 2-[3-(3-thienyl)phenoxy]ethoxyacetic acid was dissolved in 7 ml of tetrahydrofuran, and under ice cooling, 110 μl of methyl chloroformate and 200 μl of triethylamine were added. After the mixture was stirred with cooling for 30 minutes, 178 μl of cyclopropylamine was added. The mixture was stirred at room temperature for 1 hour, and then ethyl ether and water were added. The organic layer separated was worked up in a customary manner to give 0.31 g of N-cyclopropyl-2-[3-(3-thienyl)phenoxy]ethoxyacetamide as a pale yellow oil.

Workup

  1. temperaturewith cooling for 30 minutes
  2. stirringThe mixture was stirred at room temperature for 1 hour
  3. customThe organic layer separated

Sources & evidence

ORD record
ord-130e8a5ac4f6486b881f46dc2c6c34f5
Source dataset
uspto-grants-1995_08
Patent number
US05439932

Reaction notes

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