Hydrochloric Acid → HCID 13373638, compound

HRID 2417788Notes

Reaction equation

HRID 2417788 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:5]2[N:6]=[C:7]([S:9]([NH2:12])(=[O:11])=[O:10])[S:8][C:4]=2[CH:3]=1.[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1.Cl>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[CH3:25][C:15]1[CH:20]=[CH:19][C:18]([S:21]([O:1][C:2]2[CH:14]=[CH:13][C:5]3[N:6]=[C:7]([S:9](=[O:11])(=[O:10])[NH2:12])[S:8][C:4]=3[CH:3]=2)(=[O:23])=[O:22])=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chloride2×HCID 68521296-Hydroxy-1,3-benzothiazole-2-sulfonamide

Product 1

HCID 13373638HCID 13373638, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred mixture of 6-hydroxy-2-benzothiazolesulfonamide (2.3 g., 0.01 mole) and 4-dimethylaminopyridine (200 mg) in pyridine (25 ml) was added p-toluenesulfonyl chloride (1.9 g, 0.01 mole). The reaction mixture was stirred at 25° C. for 21/2 hours, treated with p-toluenesulfonyl chloride (0.3 g.), stirred 1 hour then poured into ice water plus excess hydrochloric acid. The product was extracted into ether, washed with water, dried over magnesium sulfate, concentrated to dryness and chromatographed on silica (150 g., 70-230 mesh) eluting with ethyl acetate-hexane (1:1) to obtain 1.4 g. of (2-sulfamoyl-6-benzothiazolyl) 4-methylphenyl sulfonate which melts at 142° C. after recrystallization from toluene.

Workup

  1. stirringstirred 1 hour
  2. extractionThe product was extracted into ether
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to dryness
  6. customchromatographed on silica (150 g., 70-230 mesh)
  7. washeluting with ethyl acetate-hexane (1:1)
  8. customto obtain 1.4 g
  9. customof (2-sulfamoyl-6-benzothiazolyl) 4-methylphenyl sulfonate which melts at 142° C. after recrystallization from toluene

Sources & evidence

ORD record
ord-6008e690b12443a8831396be6d2bd30d
Source dataset
uspto-grants-1984_09
Patent number
US04470991

Reaction notes

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