Triethylamine → N-(4-Cyano-3-methyl-1,2-thiazol-5-yl)butanamide

HRID 1782129Notes

Reaction equation

HRID 1782129 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4]([CH3:7])[C:3]=1[C:8]#[N:9].CCN(CC)CC.[C:17](Cl)(=[O:21])[CH2:18][CH2:19][CH3:20]>C(Cl)Cl>[C:8]([C:3]1[C:4]([CH3:7])=[N:5][S:6][C:2]=1[NH:1][C:17](=[O:21])[CH2:18][CH2:19][CH3:20])#[N:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 14977025-amino-3-methylisothiazole-4-carbonitrile

Product 1

HCID 57587941N-(4-Cyano-3-methyl-1,2-thiazol-5-yl)butanamideYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-amino-3-methylisothiazole-4-carbonitrile (method 4) (5.31 g, 38.2 mmol) in DCM (200 mL) at 0° C., NEt3 (5 g, 50 mmol) was added followed by the dropwise addition of a solution of the butyryl chloride (4.88 g, 45.8 mmol) in DCM (50 mL). After the completion of the addition the reaction mixture was allowed to warm to r.t. and stirred overnight. The reaction mixture was washed with water (100 mL), 1N HCl (100 mL), brine (200 mL) and dried over Na2SO4. Concentration of the DCM layer provided the crude product which was triturated from DCM/hexanes ( 1/10) and filtered off to isolate the pure N-(4-cyano-3-methyl-isothiazol-5-yl)-butyramide (7.57 g, 95%) as an orange solid.

Workup

  1. additionAfter the completion of the addition the reaction mixture
  2. washThe reaction mixture was washed with water (100 mL), 1N HCl (100 mL), brine (200 mL)
  3. dry with materialdried over Na2SO4
  4. customConcentration of the DCM layer provided the crude product which
  5. customwas triturated from DCM/hexanes ( 1/10)
  6. filtrationfiltered off

Sources & evidence

ORD record
ord-359c7aa4a0d249c2b93218dff21924ea
Source dataset
uspto-grants-2009_03
Patent number
US07498333B2

Reaction notes

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