Sodium Carbonate → 2-Benzothiazolesulfinamide, N,N-dimethyl-

HRID 328327Notes

Reaction equation

HRID 328327 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].C(=O)(O)[O-].[Na+].[CH3:12][N:13]([CH3:24])[S:14][C:15]1[S:16][C:17]2[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=2[N:19]=1.Cl[O-:26].[Na+].[OH-].[Na+].Cl[O-]>O>[CH3:12][N:13]([CH3:24])[S:14]([C:15]1[S:16][C:17]2[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=2[N:19]=1)=[O:26]

Participants

8

Reactant 6

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 61739HypochloriteHCID 516892Sodium BicarbonateHCID 14345394HCID 14345394, compoundHCID 23665760Sodium Hypochlorite2×

Product 1

HCID 1179832-Benzothiazolesulfinamide, N,N-dimethyl-Yield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10 parts of sodium carbonate and 4 parts of sodium bicarbonate are added to a well stirred suspension of 63 parts 2-N,N-dimethylbenzothiazole-sulphenamide in 130 parts of water. 170 parts by volume of a solution of sodium hypochlorite titrating 177 g. of NaClO and 3 g. of free caustic soda per liter are then slowly introduced, in about 5 hours and keeping the temperature within the range from 25° C. to below 30° C. The excess of hypochlorite is controlled by starchiodide paper. After introduction, the mixture is stirred for a further hour. The creamy white precipitate obtained is filtered off, washed until the washings are neutral and dried at 60° C. The 2-N,N-dimethyl-benzothiazole-sulphinamide melting at 121°-122° C., free from dibenzothiazyl disulphide, is obtained with a yield of 90%.

Workup

  1. customfrom 25° C. to below 30° C
  2. stirringAfter introduction, the mixture is stirred for a further hour
  3. customThe creamy white precipitate obtained
  4. filtrationis filtered off
  5. washwashed until the washings
  6. customdried at 60° C

Sources & evidence

ORD record
ord-15281c2d5e584f65b435eb678d0fefec
Source dataset
uspto-grants-1977_04
Patent number
US04017506

Reaction notes

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