Sodium Sulfate → HCID 67496094, compound

HRID 1022475Notes

Reaction equation

HRID 1022475 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[O:12]1[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]1.[O-]S([O-])(=O)=O.[Na+].[Na+]>C(O)(=O)C>[Br:11][C:8]1[CH:9]=[CH:10][C:2]([NH:1][CH:15]2[CH2:16][CH2:17][O:12][CH2:13][CH2:14]2)=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 798582-Amino-5-bromobenzoic acidHCID 121599Tetrahydro-4H-pyran-4-one

Product 1

HCID 67496094HCID 67496094, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 5 g of 2-amino-5-bromobenzoic acid, 9.27 g of tetrahydro-4H-pyran-4-one and 32 g of Na2SO4 in 50 ml of acetic acid is stirred overnight at room temperature. The reaction mixture is filtered. A further 9.27 g of tetrahydro-4H-pyran-4-one and 32 g of Na2SO4 are added and the resulting mixture is stirred overnight at room temperature. This mixture is filtered and 9.81 g of NaBH(OAc)3 are added. The resulting mixture is allowed to cool to room temperature over 2 hours. The reaction medium is evaporated under reduced pressure and the residue is taken up in EtOAc. It is washed with aqueous 1N HCl solution. The organic phase is dried over Na2SO4, filtered and evaporated under reduced pressure to give 3.35 g of the expected product.

Workup

  1. filtrationThe reaction mixture is filtered
  2. additionA further 9.27 g of tetrahydro-4H-pyran-4-one and 32 g of Na2SO4 are added
  3. stirringthe resulting mixture is stirred overnight at room temperature
  4. filtrationThis mixture is filtered
  5. addition9.81 g of NaBH(OAc)3 are added
  6. temperatureto cool to room temperature over 2 hours
  7. customThe reaction medium is evaporated under reduced pressure
  8. washIt is washed with aqueous 1N HCl solution
  9. dry with materialThe organic phase is dried over Na2SO4
  10. filtrationfiltered
  11. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-4f1a2a208a6447678a7e1b4cd9ca8f3c
Source dataset
uspto-grants-2014_05
Patent number
US08722659B2

Reaction notes

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