Water → HCID 2826591, compound

HRID 1154509Notes

Reaction equation

HRID 1154509 reaction equation
[S:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[CH:3][CH2:2]1.[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1.C[O-:21].[Na+].O>CN(C)C=O>[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[C:2]2[C:3](=[O:21])[NH:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[S:1]2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 77264-ChlorobenzaldehydeHCID 30889971,4-BenzothiazineHCID 10942334Sodium Methoxide

Product 1

HCID 2826591HCID 2826591, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2H-1,4-benzothiazine-3(4H-one (2 g) and 4-chlorobenzaldehyde (2.6 g) in dimethylformamide (15 ml) was treated with sodium methylate (0.98 g). The temperature of the mixture rose spontaneously. After cooling to room temperature, the reaction mixture was stirred and heated at 110° C. with a continuous removal of a low boiling substance for 3 hours. The reaction mixture was cooled to 30° C., and poured onto 100 ml of iced water. The resulted yellow solid was filtered and recrystallized from a mixture of dimethylformamide and isopropyl alcohol. 2-(4-Chlorophenylmethylidene)-2H-1,4-benzothiazine-3(4H)-one (3.3 g) was obtained as yellow crystals. m.p. 245-248° C.

Workup

  1. temperatureheated at 110° C. with a continuous removal of a low boiling substance for 3 hours
  2. temperatureThe reaction mixture was cooled to 30° C.
  3. filtrationThe resulted yellow solid was filtered
  4. customrecrystallized from a mixture of dimethylformamide and isopropyl alcohol

Sources & evidence

ORD record
ord-487001485cbd4284835b95f28ff1e4d0
Source dataset
uspto-grants-1984_12
Patent number
US04490292

Reaction notes

Loading…