2-Cyanoethanethioamide → (2'-Amino-4'-methyl-4,5'-bi-1,3-thiazol-2-yl)acetonitrile

HRID 1715290Notes

Reaction equation

HRID 1715290 reaction equation
C([NH:4][C:5]1[S:6][C:7]([C:11]2[N:12]=[C:13]([C:16](NCC=C)=O)[S:14][CH:15]=2)=[C:8]([CH3:10])[N:9]=1)(=O)C.[C:22](CC(N)=S)#[N:23]>CCO>[NH2:4][C:5]1[S:6][C:7]([C:11]2[N:12]=[C:13]([CH2:16][C:22]#[N:23])[S:14][CH:15]=2)=[C:8]([CH3:10])[N:9]=1

Participants

4

Reactant 2

HCID 14162772-CyanoethanethioamideHCID 119612582'-(Acetylamino)-N-allyl-4'-methyl-4,5'-bi-1,3-thiazole-2-carboxamide2×

Product 1

HCID 59465553(2'-Amino-4'-methyl-4,5'-bi-1,3-thiazol-2-yl)acetonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(2-Amino-4-methyl-1,3-thiazol-5-yl)-2-bromo ethanone, hydrobromide salt (Intermediate 2) (116.97 mg; 0.50 mmol; 1 eq.) and 2-cyanothioacetamide (Aldrich) (50.1 mg; 0.50 mmol; 1 eq.) are dissolved in EtOH (5 ml). The mixture is stirred at rt overnight. Solvents are evaporated, affording a yellow-orange solid which is purified by flash chromatography (CHCl3/EtOH gradient, from 50:1 to 10:1). (2′-amino-4′-methyl-4,5′-bi-1,3-thiazol-2-yl)acetonitrile is isolated as an orange solid. (71.6 mg; 61%). 1H NMR (DMSO-d6, 300 MHz) δ 2.41 (s, 3H), 4.62 (s, 2H), 7.87 (s, 1H), 9.23 (br s, 2H). M− (ESI): 235.04; M+ (ESI): 237.06. HPLC (method A), Rt: 1.16 min (purity: 98.3%).

Workup

  1. customSolvents are evaporated
  2. customaffording a yellow-orange solid which
  3. customis purified by flash chromatography (CHCl3/EtOH gradient, from 50:1 to 10:1)

Sources & evidence

ORD record
ord-ecf0e9f777f74fbda92b76b0a9681f9a
Source dataset
uspto-grants-2010_09
Patent number
US07799814B2

Reaction notes

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