Formaldehyde → 7-chloro-4-(4-chlorophenyl)-2-(hydroxymethyl)-5H-pyrido[3,4-b][1,4]benzothiazin-3(2H)-one

HRID 615702Notes

Reaction equation

HRID 615702 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:10][C:9]3=[CH:11][NH:12][C:13](=[O:22])[C:14]([C:15]4[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=4)=[C:8]3[NH:7][C:6]=2[CH:23]=1.[OH-:24].[Na+].[CH2:26]=O>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:10][C:9]3=[CH:11][N:12]([CH2:26][OH:24])[C:13](=[O:22])[C:14]([C:15]4[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=4)=[C:8]3[NH:7][C:6]=2[CH:23]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 204269017-chloro-4-(4-chlorophenyl)-5H-pyrido[3,4-b][1,4]-benzothiazin-3(2H)-one

Product 1

HCID 204269037-chloro-4-(4-chlorophenyl)-2-(hydroxymethyl)-5H-pyrido[3,4-b][1,4]benzothiazin-3(2H)-oneYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 5.0 g. of 7-chloro-4-(4-chlorophenyl)-5H-pyrido[3,4-b][1,4]-benzothiazin-3(2H)-one (13.8 mmol.) in 50 ml. dimethylformamide was added 30 ml. of a 5% sodium hydroxide solution (37.5 mmol.) and the resulting suspension was heated on a steam bath until the solid dissolved. To the resulting solution was then added 50 ml. of 36% formaldehyde solution (60.0 mmol.), and the resulting reaction mixture was heated on a steam bath for 30 minutes, then cooled to room temmperature, yielding a yellow precipitate. The mixture was filtered, and the collected precipitate was washed with water and dried under vacuum at room temperature to yield 7-chloro-4-(4-chlorophenyl)-2-(hydroxymethyl)-5H-pyrido[3,4-b][1,4]benzothiazin-3(2H)-one as a yellow solid (4.7 g.; 87% yield) having the structural formula, ##STR13## a melting point of 295°-300° C. (with decomposition) and the following elemental analysis:

Workup

  1. dissolutiondissolved
  2. additionTo the resulting solution was then added 50 ml
  3. temperaturewas heated on a steam bath for 30 minutes
  4. temperaturecooled to room temmperature
  5. customyielding a yellow precipitate
  6. filtrationThe mixture was filtered
  7. washthe collected precipitate was washed with water
  8. customdried under vacuum at room temperature

Sources & evidence

ORD record
ord-90b89a77fdac4d3a8e39a7ab6b969226
Source dataset
uspto-grants-1985_02
Patent number
US04500708

Reaction notes

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