Triethylamine → 2-(methylthio)-N-(2-methylpent-3-yn-2-yl)acetamide

HRID 217155Notes

Reaction equation

HRID 217155 reaction equation
C(N([CH2:6][CH3:7])CC)C.Cl.[NH2:9][C:10]([CH3:15])([CH3:14])[C:11]#[C:12][CH3:13].CC[C:18](O)=[S:19].C1C=CC2N([OH:30])N=NC=2C=1>CN(C=O)C.O.C(Cl)CCl>[CH3:18][S:19][CH2:6][C:7]([NH:9][C:10]([CH3:15])([C:11]#[C:12][CH3:13])[CH3:14])=[O:30]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 219231292-Methylpent-3-yn-2-amine hydrochlorideHCID 178460587HCID 178460587, compound

Product 1

HCID 860149882-(methylthio)-N-(2-methylpent-3-yn-2-yl)acetamide

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

Triethylamine (1.84 ml) was added to a stirred solution of 4-amino-4-methyl -pent-2-yne hydrochloride (1.278 g) in DMF (5 ml) at ambient temperature giving a white suspension. Methylthioacetic acid (1.0 g) was dissolved in DMF (5 ml) then added to the amine followed by HOBT (1.27 g) and finally EDC (1.806 g). The white suspension was stirred at room temperature for 6 hours and stored overnight. Water was added and the aqueous phase was extracted with diethyl ether. The organic phases were combined, successively washed with water and dried over magnesium sulphate, filtered and evaporated under reduced pressure to give 2-(methylthio)-N-(2-methylpent-3-yn -2-yl)acetamide as a yellow orange solid (1.9 g).

Workup

  1. customgiving a white suspension
  2. waitstored overnight
  3. extractionthe aqueous phase was extracted with diethyl ether
  4. washsuccessively washed with water
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-3cb2954a609a4cd68295d3d763811755
Source dataset
uspto-grants-2012_06
Patent number
US08193361B2

Reaction notes

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