Sulfuric Acid → HCID 59603069, compound

HRID 2068708Notes

Reaction equation

HRID 2068708 reaction equation
C([O:8][C:9]1[C:10]([CH3:27])=[CH:11][C:12]2[S:16][C:15]([NH:17]C(=O)C3C=CC=CC=3)=[N:14][C:13]=2[CH:26]=1)C1C=CC=CC=1.OS(O)(=O)=O.C([O-])([O-])=O.[Na+].[Na+]>>[NH2:17][C:15]1[S:16][C:12]2[CH:11]=[C:10]([CH3:27])[C:9]([OH:8])=[CH:26][C:13]=2[N:14]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 59603103HCID 59603103, compound

Product 1

HCID 59603069HCID 59603069, compoundYield 70%

Conditions

Temperature
140 °C

Procedure

To an ice-cooled solution of N-(5-benzyloxy-6-methyl-benzothiazol-2-yl)-benzamide (0.60 g, 1.60 mmol) was added 70% aq. H2SO4 (5-6 mL). The resulting mixture was heated to 140° C. for 1 h. After completion of reaction (TLC monitoring), the reaction mixture was basified with aq. Na2CO3 solution (pH 10) and extracted with EtOAc (2×300 mL). The organic layers were combined and washed with brine solution, dried over Na2SO4, filtered and concentrated to obtain the desired product as a white solid (0.20 g, 70%). MS: 181.16 (M+H)+.

Workup

  1. customAfter completion of reaction (TLC monitoring)
  2. extractionextracted with EtOAc (2×300 mL)
  3. washwashed with brine solution
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1b1485458fb24d6aac72708e2512292d
Source dataset
uspto-grants-2012_10
Patent number
US08299065B2

Reaction notes

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