Ammonium Chloride → HCID 22742108, compound

HRID 48175Notes

Reaction equation

HRID 48175 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4]([CH3:7])[C:3]=1[Cl:8].C[O-].[Na+].[CH3:12][C:13]([CH3:32])([CH3:31])[CH2:14][C:15]1[O:16][C:17]2[CH:23]=[CH:22][C:21]([C:24]([F:30])([CH3:29])[C:25](OC)=[O:26])=[CH:20][C:18]=2[N:19]=1.[Cl-].[NH4+]>O1CCCC1.O>[Cl:8][C:3]1[C:4]([CH3:7])=[N:5][S:6][C:2]=1[NH:1][C:25](=[O:26])[C:24]([C:21]1[CH:22]=[CH:23][C:17]2[O:16][C:15]([CH2:14][C:13]([CH3:31])([CH3:12])[CH3:32])=[N:19][C:18]=2[CH:20]=1)([F:30])[CH3:29]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 112405714-Chloro-3-methyl-1,2-thiazol-5-amineHCID 22742109Methyl 2-[2-(2,2-dimethylpropyl)benzoxazol-5-yl]-2-fluoropropionate

Product 1

HCID 22742108HCID 22742108, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

5-Amino-4-chloro-3-methylisothiazole (0.28 g, 0.00188 mol) was added to a suspension of sodium methoxide (0.24 g, 0.004 mol) in tetrahydrofuran (6 ml) and the mixture was stirred at room temperature for 20 minutes. A solution of methyl 2-[2-(2,2-dimethylpropyl)benzoxazol-5-yl]-2-fluoropropionate (0.50 g, 0.00171 mol) in tetrahydrofuran (2 ml) was added, dropwise, and the mixture was stirred at room temperature for 3 hours. The mixture was diluted with water, acidified with saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic extract was dried over anhydrous magnesium sulfate, filtered and the filtrate was evaporated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with ethyl acetate:hexane 12:88, to give the desired product (0.575 g) as a pale yellow gum.

Workup

  1. stirringdropwise, and the mixture was stirred at room temperature for 3 hours
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe filtrate was evaporated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel
  8. washeluting with ethyl acetate:hexane 12:88

Sources & evidence

ORD record
ord-143452fe025747289e2692fe2abbeb5f
Source dataset
uspto-grants-2004_03
Patent number
US06703347B2

Reaction notes

Loading…