Dimethylformamide → 6-Bromo-2-chlorobenzothiazole

HRID 70136

Reaction equation

HRID 70136 reaction equation
CN(C=O)C.P(Cl)(Cl)([Cl:8])=O.[Br:11][C:12]1[CH:21]=[CH:20][C:15]2[NH:16][C:17](=O)[S:18][C:14]=2[CH:13]=1.C([O-])([O-])=O.[K+].[K+]>O>[Br:11][C:12]1[CH:21]=[CH:20][C:15]2[N:16]=[C:17]([Cl:8])[S:18][C:14]=2[CH:13]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium Carbonate2×HCID 24813Phosphorus oxychlorideHCID 1884446-Bromo-2,3-dihydro-1,3-benzothiazol-2-one

Product 1

HCID 20498716-Bromo-2-chlorobenzothiazoleYield 95.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

DMF (0.807 mL, 10.4 mmol) was added to phosphorous oxychloride (8.10 mL, 86.9 mmol), and the reaction mixture was stirred for 15 min. 6-bromobenzo[d]thiazol-2(3H)-one (2.00 g, 8.69 mmol) was added and the reaction mixture was heated to 100° C. overnight. Upon cooling to rt, the reaction mixture was slowly added to a solution of K2CO3 (75 g) in water (200 mL) while maintaining the temperature below 35° C. Additional K2CO3 was added in order to maintain the pH above 10. Upon complete addition, the mixture was allowed to stir for 1 h. The solid was collected by filtration, washed with water (2×25 mL), and air dried. Further drying in a vacuum oven gave 2.06 g (95%) of the desired product as a brown solid. The material was used without further purification. LC-MS: RT=9.94 min., compound does not ionize.

Workup

  1. temperatureUpon cooling to rt
  2. temperaturewhile maintaining the temperature below 35° C
  3. temperatureto maintain the pH above 10
  4. additionUpon complete addition
  5. stirringto stir for 1 h
  6. filtrationThe solid was collected by filtration
  7. washwashed with water (2×25 mL), and air
  8. customdried
  9. customFurther drying in a vacuum oven

Sources & evidence

ORD record
ord-0cbfa0965f994ce7b31dbfe2762142bb
Source dataset
uspto-grants-2014_09
Patent number
US08822472B2

Linked notes

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