2,6-Lutidine → HCID 178527168, compound

HRID 437125Notes

Reaction equation

HRID 437125 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]2[NH:6][C:7](=O)[NH:8][S:9](=[O:11])(=[O:10])[C:4]=2[CH:3]=1.N1C(C)=CC=CC=1C.P(Cl)(Cl)([Cl:25])=O>>[Cl:25][C:7]1[NH:8][S:9](=[O:11])(=[O:10])[C:4]2[CH:3]=[C:2]([Cl:1])[CH:14]=[CH:13][C:5]=2[N:6]=1

Participants

4

Reactant 3

HCID 79372,6-LutidineHCID 24813Phosphorus oxychlorideHCID 103315247-chloro-2H-benzo[e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxide

Product 1

HCID 178527168HCID 178527168, compound

Procedure

To a stirred suspension of 8.0 g of 7-chloro-3,4-dihydro-3-oxo-2H-1,2,4-benzothiadiazine 1,1-dioxide in 80 g of phosphorus oxychloride is added dropwise 7.4 g of 2,6-lutidine, while the mixture is cooled in an ice bath. After the addition, the mixture is heated under reflux for 12 hours and concentrated under reduced pressure. To the residue is added 400 ml of ice water and the resulting mixture is stirred for 30 minutes. The crystalline precipitate is collected by suction filtration, washed with water and then with 2-propanol, and recrystallized from 2-propanol to afford the desired product, m.p. 242°-244° C.

Workup

  1. temperaturewhile the mixture is cooled in an ice bath
  2. additionAfter the addition
  3. temperaturethe mixture is heated
  4. temperatureunder reflux for 12 hours
  5. concentrationconcentrated under reduced pressure
  6. additionTo the residue is added 400 ml of ice water
  7. filtrationThe crystalline precipitate is collected by suction filtration
  8. washwashed with water
  9. customwith 2-propanol, and recrystallized from 2-propanol

Sources & evidence

ORD record
ord-18e684fbb7be49d5bcdbfee8be662646
Source dataset
uspto-grants-1977_06
Patent number
US04029780

Reaction notes

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