Triethylamine → HCID 86253095, compound

HRID 2174718Notes

Reaction equation

HRID 2174718 reaction equation
[NH:1]1[CH2:3][CH:2]1[C:4]([O:6][CH3:7])=[O:5].C(N(CC)CC)C.[Cl:15][C:16]1[S:20][C:19]([C:21](Cl)=[O:22])=[CH:18][CH:17]=1>C(Cl)Cl>[Cl:15][C:16]1[S:20][C:19]([C:21]([N:1]2[CH2:3][CH:2]2[C:4]([O:6][CH3:7])=[O:5])=[O:22])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 534940Methyl Aziridine-2-carboxylateHCID 5892235-Chlorothiophene-2-carbonyl Chloride

Product 1

HCID 86253095HCID 86253095, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 4.40 g (43.5 mmol) methyl aziridine-2-carboxylate and 13.5 ml (97.3 mmol) triethylamine in 30 ml methylene chloride is combined with 8.80 g (48.6 mmol) 5-chlorothiophenecarboxylic acid chloride in 30 ml methylene chloride while cooling with ice and subsequently after removal of the cooling bath stirred for 3 h at room temperature. Then the mixture is diluted with water, extracted with methylene chloride, dried with sodium sulphate, concentrated and purified by chromatography (silica gel, petroleum ether/ethyl acetate 80/15->80/20) to obtain the slightly contaminated title compound.

Workup

  1. temperaturewhile cooling with ice
  2. customsubsequently after removal of the cooling bath
  3. additionThen the mixture is diluted with water
  4. extractionextracted with methylene chloride
  5. dry with materialdried with sodium sulphate
  6. concentrationconcentrated
  7. custompurified by chromatography (silica gel, petroleum ether/ethyl acetate 80/15->80/20)

Sources & evidence

ORD record
ord-5ab93823641447608918b5d8df6f6377
Source dataset
uspto-grants-2015_06
Patent number
US09062034B2

Reaction notes

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