Water → HCID 18984441, compound

HRID 1198443Notes

Reaction equation

HRID 1198443 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[S:13][C:12]3[CH:14]=[CH:15][C:16]4[C:21]([C:11]=3[NH:10][CH2:9]2)=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:4][CH:3]=1.C(=O)([O-])O.[Na+].O.[C:28](Cl)(=[O:31])[CH:29]=[CH2:30]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[S:13][C:12]3[CH:14]=[CH:15][C:16]4[C:21]([C:11]=3[N:10]([C:28](=[O:31])[CH:29]=[CH2:30])[CH2:9]2)=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 13140Acryloyl chlorideHCID 516892Sodium BicarbonateHCID 189844023-(4-chlorophenyl)-2,3-dihydro1H-naphtho[2,1-b][1,4]thiazine

Product 1

HCID 18984441HCID 18984441, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 3-(4-chlorophenyl)-2,3-dihydro-1H-naphtho[2,1-b][1,4]thiazine (1.50 g), sodium hydrogen carbonate (1.0 g), methylene chloride (30 ml) and water (15 ml) is added dropwise with stirring a solution of acryloyl chloride (0.90 g) in methylene chloride (10 ml) under ice cooling. The mixture is stirred at room temperature for 3 hours. The organic layer is separated, washed, dried and distilled to remove the solvent. The residue is chromatographed on silica gel (toluene: acetone=50:1) to give 3-(4-chlorophenyl)-1-propenoyl-2,3-dihydro-1H-naphtho[2,1-b][1,4]thiazine (1.37 g, 78%) as powder.

Workup

  1. additionis added dropwise
  2. customThe organic layer is separated
  3. washwashed
  4. customdried
  5. distillationdistilled
  6. customto remove the solvent
  7. customThe residue is chromatographed on silica gel (toluene: acetone=50:1)

Sources & evidence

ORD record
ord-795a866274d749dfa4b87ef2b70f34bb
Source dataset
uspto-grants-1994_01
Patent number
US05281592

Reaction notes

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