5-Amino-4-chloro-3-ethylisothiazole → HCID 22742112, compound

HRID 48173Notes

Reaction equation

HRID 48173 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4]([CH2:7][CH3:8])[C:3]=1[Cl:9].C[O-].[Na+].[CH3:13][CH:14]([CH3:31])[CH2:15][C:16]1[S:17][C:18]2[CH:24]=[CH:23][C:22]([CH:25]([CH3:30])[C:26](OC)=[O:27])=[CH:21][C:19]=2[N:20]=1>O1CCCC1.[Cl-].[NH4+]>[Cl:9][C:3]1[C:4]([CH2:7][CH3:8])=[N:5][S:6][C:2]=1[NH:1][C:26](=[O:27])[CH:25]([C:22]1[CH:23]=[CH:24][C:18]2[S:17][C:16]([CH2:15][CH:14]([CH3:13])[CH3:31])=[N:20][C:19]=2[CH:21]=1)[CH3:30]

Participants

6

Reactant 3

HCID 98774685-Amino-4-chloro-3-ethylisothiazoleHCID 10942334Sodium MethoxideHCID 22742088Methyl 2-[2-(2-methylpropyl)benzothiazol-5-yl]propionate

Product 1

HCID 22742112HCID 22742112, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 25517Ammonium ChlorideSolvent

Procedure

5-Amino-4-chloro-3-ethylisothiazole (0.81 g, 0.005 mol) was added to a suspension of sodium methoxide (0.56 g, 0.010 mol) in tetrahydrofuran (5 ml) and the mixture stirred at room temperature for 25 minutes. A solution of methyl 2-[2-(2-methylpropyl)benzothiazol-5-yl]propionate (1.15 g, 0.004 mol) in tetrahydrofuran (4 ml) was added dropwise and the mixture stirred at room temperature for 1½ hours. The mixture was diluted with saturated aqueous ammonium chloride solution and extracted with dichloromethane. The organic extract was dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated in vacuo. Trituration with diethyl ether gave the desired product (1.06 g).

Workup

  1. stirringthe mixture stirred at room temperature for 1½ hours
  2. extractionextracted with dichloromethane
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-6c19937bc9344f95a37626e2dfe904b9
Source dataset
uspto-grants-2004_03
Patent number
US06703347B2

Reaction notes

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