2-Methylpyridine → Sodium 4-(benzothiazol-2-yl)phenylsulphamate

HRID 1636566Notes

Reaction equation

HRID 1636566 reaction equation
N1C=CC=CC=1C.Cl[S:9]([OH:12])(=[O:11])=[O:10].[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[S:21][C:22]3[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=3[N:24]=2)=[CH:16][C:15]=1I.C(=O)([O-])[O-].[Na+:34].[Na+]>>[S:21]1[C:22]2[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=2[N:24]=[C:20]1[C:17]1[CH:18]=[CH:19][C:14]([NH:13][S:9](=[O:11])(=[O:10])[O-:12])=[CH:15][CH:16]=1.[Na+:34]

Participants

5

Reactant 4

HCID 79752-MethylpyridineHCID 10340Sodium CarbonateHCID 24638Chlorosulfonic acidHCID 384526Benzenamine, 4-(2-benzothiazolyl)-2-iodo-

Product 1

HCID 23717892Sodium 4-(benzothiazol-2-yl)phenylsulphamate

Conditions

Temperature
50 °C

Procedure

To anhydrous 2-picoline (1.05 g, 11 mmol) was slowly added dropwise chlorsulphonic acid (0.26 g, 2.21 mmol) below 10° C. then 2-(4'-amino-3'-iodophenyl)benzothiazole (0.5 g, 2.21 mmol). The mixture was heated to 50° C. with stirring for 1 hour. After leaving to stand for 2 hours at room temperature, 6 ml of 10% aqueous sodium carbonate was added. The resulting mixture was stirred for 40 minutes at room temperature and concentrated under reduced pressure. The precipitate was filtered off, washed carefully with cold water and treated with hot chlorform. Golden crystals were afforded (0.62 g, 85.5%), m.p. 288-290° C.

Workup

  1. customAfter leaving
  2. waitto stand for 2 hours at room temperature
  3. stirringThe resulting mixture was stirred for 40 minutes at room temperature
  4. concentrationconcentrated under reduced pressure
  5. filtrationThe precipitate was filtered off
  6. washwashed carefully with cold water
  7. additiontreated with hot chlorform
  8. customGolden crystals were afforded (0.62 g, 85.5%), m.p. 288-290° C.

Sources & evidence

ORD record
ord-238ae6d3d5b64f388881ec0f478e52b2
Source dataset
uspto-grants-2000_03
Patent number
US06034246

Reaction notes

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