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

HRID 563887Notes

Reaction equation

HRID 563887 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) giving a white suspension. Methylthioacetic acid (1.0 g) in DMF (5 ml) was then added to the amine followed by the HOBT (1.27 g) and finally EDC (1.806 g). The white suspension was stirred at ambient temperature for 6 hours, and stored for 18 hours. Water was added and the aqueous phase was extracted with diethyl ether. The organic phases were combined, washed with water and dried over magnesium sulphate then filtered and evaporated 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 for 18 hours
  3. extractionthe aqueous phase was extracted with diethyl ether
  4. washwashed with water
  5. dry with materialdried over magnesium sulphate
  6. filtrationthen filtered
  7. customevaporated

Sources & evidence

ORD record
ord-ebacb50a592d4e359ac795237b12617b
Source dataset
uspto-grants-2011_11
Patent number
US08067592B2

Reaction notes

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