Hydrochloric Acid → HCID 20492731, compound

HRID 434495Notes

Reaction equation

HRID 434495 reaction equation
N12CCCN=C1CCCCC2.[Cl:12][C:13]1[CH:26]=[CH:25][C:16]2[N:17]([CH3:24])[C:18](=[O:23])[CH2:19][S:20](=[O:22])(=[O:21])[C:15]=2[CH:14]=1.[F:27][C:28]1[CH:33]=[CH:32][C:31]([N:34]=[C:35]=[O:36])=[CH:30][CH:29]=1.Cl>CN(C)C=O>[Cl:12][C:13]1[CH:26]=[CH:25][C:16]2[N:17]([CH3:24])[C:18](=[O:23])[CH:19]([C:35](=[O:36])[NH:34][C:31]3[CH:32]=[CH:33][C:28]([F:27])=[CH:29][CH:30]=3)[S:20](=[O:22])(=[O:21])[C:15]=2[CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 709554-Fluorophenyl isocyanateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 20492773HCID 20492773, compound

Product 1

HCID 20492731HCID 20492731, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 1,8-diazabicyclo-[5,4,0]undec-7-ene (14.12 g) in dimethylformamide (111 ml) was added, dropwise in 10 minutes, a solution of 7-chloro-4-methyl-2H-1,4-benzothiazin-3(4H)one 1,1-dioxide (22.8 g) and 4-fluorophenylisocyanate (12.82 g) in dimethylformamide (111.4 ml) at room temperature. After being stirred for one hour, the mixture was poured into 1% hydrochloric acid (1 l). The separated solids were collected by filtration and washed with water. The wet solids were dissolved in ethyl acetate. The mixture was washed with 1% hydrochloric acid, with water, dried over magnesium sulfate, and evaporated under reduced pressure. The residue was crystallized from diethyl ether to yield 24.3 g of 7-chloro-2-(4-fluorophenylcarbamoyl)-4-methyl-2H-1,4-benzothiazin-3(4H)one 1,1-dioxide.

Workup

  1. customat room temperature
  2. filtrationThe separated solids were collected by filtration
  3. washwashed with water
  4. dissolutionThe wet solids were dissolved in ethyl acetate
  5. washThe mixture was washed with 1% hydrochloric acid, with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-f5ed8f6fd06e428eb5c6149592963611
Source dataset
uspto-grants-1983_08
Patent number
US04397849

Reaction notes

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