Water → 2-(4-chlorophenyl)-4-acryloyl-3,4-dihyro-2H-1,4-benzothiazine

HRID 5824Notes

Reaction equation

HRID 5824 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][NH:12][C:11]3[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=3[S:9]2)=[CH:4][CH:3]=1.C(=O)([O-])O.[Na+].O.[C:24](Cl)(=[O:27])[CH:25]=[CH2:26]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:13][N:12]([C:24](=[O:27])[CH:25]=[CH2:26])[C:11]3[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=3[S:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 13140Acryloyl chlorideHCID 516892Sodium BicarbonateHCID 130715242-(4-chlorophenyl)-3,4-dihydro2H-1,4-benzothiazine

Product 1

HCID 700422142-(4-chlorophenyl)-4-acryloyl-3,4-dihyro-2H-1,4-benzothiazineYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 2-(4-chlorophenyl)-3,4-dihydro-2H-1,4-benzothiazine (9.62 g), sodium hydrogen carbonate (6.0 g), methylene chloride (100 ml) and water (50 ml) is added dropwise with stirring a solution of acryloyl chloride (5.0 g) in methylene chloride (20 ml) under ice cooling over a period of about 30 minutes. The mixture is stirred at room temperature for 3 hours, and the organic layer is washed and dried. After the solvent is distilled off, the resulting crystals are washed with n-hexane to give 2-(4-chlorophenyl)-4-acryloyl-3,4-dihyro-2H-1,4-benzothiazine (10.76 g, yield 93%).

Workup

  1. additionis added dropwise
  2. washthe organic layer is washed
  3. customdried
  4. distillationAfter the solvent is distilled off
  5. washthe resulting crystals are washed with n-hexane

Sources & evidence

ORD record
ord-d89b6b0a42ba47e2b52fd965ff8e6b9b
Source dataset
uspto-grants-1993_09
Patent number
US05246929

Reaction notes

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