Hydrochloric Acid → Benzoic acid 6-bromo-3-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-naphthalen-2-yl ester

HRID 643896Notes

Reaction equation

HRID 643896 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([OH:20])[C:8]([N:12]3[S:16](=[O:18])(=[O:17])[NH:15][C:14](=[O:19])[CH2:13]3)=[CH:9]2)=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[C:27](Cl)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C([O-])(O)=O.[Na+].Cl>CO.CN(C=O)C>[Br:1][C:2]1[CH:11]=[C:10]2[C:5](=[CH:4][CH:3]=1)[CH:6]=[C:7]([O:20][C:27](=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:8]([N:12]1[CH2:13][C:14](=[O:19])[NH:15][S:16]1(=[O:18])=[O:17])=[CH:9]2

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 516892Sodium BicarbonateHCID 177517615-(7-Bromo-3-hydroxynaphthalen-2-yl)-1,1-dioxo-1,2,5-thiadiazolidin-3-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 86624016Benzoic acid 6-bromo-3-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-naphthalen-2-yl ester

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(7-bromo-3-hydroxynaphthalen-2-yl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (3) (0.998 g, 2.8 mmol) in MeOH is added KHCO3 (5.6 mL, 0.5M). To this salt in DMF (25 mL) at 0° C. is added potassium t-butoxide (2.94 mL, 1M). The reaction mixture is stirred for 1 min before benzoyl chloride (0.357 mL, 3.08 mmol) is added and the mixture is stirred for 1 min. Sat. NaHCO3 solution is added and it is acidified with 1 N HCl solution. The mixture is extracted with EtOAc, washed with brine and dried with Na2SO4. The organic layer is concentrated to give the title compound.

Workup

  1. additionis added
  2. extractionThe mixture is extracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried with Na2SO4
  5. concentrationThe organic layer is concentrated

Sources & evidence

ORD record
ord-5b344af121c74b649a32ade99622172a
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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