HCID 131710721, compound → HCID 12409672, compound

HRID 328970Notes

Reaction equation

HRID 328970 reaction equation
O.[C:2]([C:10]1[C:18]([S:19](=[O:22])(=[O:21])[NH2:20])=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][C:11]=1[OH:23])(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:24](C1C(S(=O)(=O)N)=CC(C(O)=O)=CC=1O)(=O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>[OH-].[Na+].C(Br)C1C=CC=CC=1>[C:2]([C:10]1[C:18]([S:19](=[O:22])(=[O:21])[NH2:20])=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][C:11]=1[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=[O:9])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 131710721HCID 131710721, compound

Product 1

HCID 12409672HCID 12409672, compound

Reagents, catalysts & solvents 2

HCID 7498Benzyl BromideSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 4-benzoyl-3-hydroxy-5-sulfamylbenzoic acid hemihydrate (3.21 g) in 0.50 N NaOH (40.0 ml), benzyl bromide (1.2 ml) is added and the mixture is stirred at room temperature for 5 hours. The mixture is left in a refrigerator for about 16 hours, and the separated sodium 4-benzoyl-3-benzyloxy-5-sulfamylbenzoate is collected by filtration and washed with a small amount of ice-cold water. The salt is dissolved in 1 N sodium hydroxide (30 ml) and the solution is added to ice-cold 1 N acetic acid (35 ml). The resulting precipitate is collected by filtration and washed with water. After drying in vacuo in the presence of P2O5, 4-benzoyl-3-benzyloxy-5-sulfamylbenzoic acid is obtained. The material is identical (IR, analysis) with the material prepared as in Example 40.

Workup

  1. waitThe mixture is left in a refrigerator for about 16 hours
  2. filtrationthe separated sodium 4-benzoyl-3-benzyloxy-5-sulfamylbenzoate is collected by filtration
  3. washwashed with a small amount of ice-cold water
  4. dissolutionThe salt is dissolved in 1 N sodium hydroxide (30 ml)
  5. additionthe solution is added to ice-cold 1 N acetic acid (35 ml)
  6. filtrationThe resulting precipitate is collected by filtration
  7. washwashed with water
  8. dry with materialAfter drying in vacuo in the presence of P2O5

Sources & evidence

ORD record
ord-a1efeed358ed4ae4bd750640be48f628
Source dataset
uspto-grants-1977_04
Patent number
US04018794

Reaction notes

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