Methyl 4-(bromomethyl)benzoate → HCID 18963773, compound

HRID 2226866Notes

Reaction equation

HRID 2226866 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.[SH:13][C:14]1[C:15]2[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:16]=2[S:17][C:18]=1[C:19]([NH2:21])=[O:20].C([O-])(O)=O.[Na+]>C1COCC1.C(OCC)(=O)C>[NH2:21][C:19]([C:18]1[S:17][C:16]2[CH:22]=[CH:23][C:24]([O:26][CH3:27])=[CH:25][C:15]=2[C:14]=1[S:13][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)=[O:20]

Participants

6

Reactant 3

HCID 256687Methyl 4-(bromomethyl)benzoateHCID 516892Sodium BicarbonateHCID 10847601HCID 10847601, compound

Product 1

HCID 18963773HCID 18963773, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 4-(bromomethyl)benzoate (479 mg, 2.09 mmol) is added to a room temperature solution of 3-mercapto-5-methoxybenzo[b]thiophene-2-carboxamide (200 mg, 0.84 mmol) in 12 mL of THF followed by NaHCO3 (351 mg, 4.18 mmol) and the reaction mixture is stirred at room temperature overnight. The reaction mixture is diluted with ethyl acetate and washed with 1N HCl, saturated NaHCO3, and brine. The organic layer is dried over MgSO4, filtered, and concentrated in vacuo. Chromatography eluting with ethyl acetate:dichloromethane (1:9 to 1:1) followed by recrystallization from ethyl acetate:hexane provides methyl 4-[[[2-(aminocarbonyl)-5-methoxybenzo[b]thien-3-yl]thio]methyl]-benzoate in 68% yield; mp=150°-152° C.

Workup

  1. washwashed with 1N HCl, saturated NaHCO3, and brine
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. washChromatography eluting with ethyl acetate:dichloromethane (1:9 to 1:1)
  6. customfollowed by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-bc1b22ec73b24a708a3ddc8fc2ac540a
Source dataset
uspto-grants-1994_09
Patent number
US05350748

Reaction notes

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