Formaldehyde → HCID 20426912, compound

HRID 615710Notes

Reaction equation

HRID 615710 reaction equation
[Br: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>[Br: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 20426909HCID 20426909, compound

Product 1

HCID 20426912HCID 20426912, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 2.0 g. of 7-bromo 4-(4-chlorophenyl)-5H-pyrido[3,4-b][1,4]benzothiazin-3(2H)-one (4.9 mmol.) in 20 ml. dimethylformamide was added 12 ml. of a 5% sodium hydroxide solution (15.0 mmol.) and the resulting suspension was heated on a steam bath until a solution formed. To the solution was then added 20 ml. of a 36% formaldehyde solution (24.0 mmol.), and the resulting reaction mixture was heated until a yellow precipitate formed. The hot reaction mixture was filtered, and the precipitate was washed well with water and dried under high vacuum at room temperature to yield 7-bromo-4-(4-chlorophenyl)-2-(hydroxymethyl)-5H-pyrido[3,4-b][1,4]benzothiazin-3(2H)-one as a yellow powder (1.1 g,; 51% yield) having the structural formula, ##STR23## a melting point of 182° C. (with decomposition) and the following elemental analysis:

Workup

  1. customformed
  2. additionTo the solution was then added 20 ml
  3. temperaturewas heated until a yellow precipitate
  4. customformed
  5. filtrationThe hot reaction mixture was filtered
  6. washthe precipitate was washed well with water
  7. customdried under high vacuum at room temperature

Sources & evidence

ORD record
ord-e1b78e01875148069b9a90f5c1c0eee4
Source dataset
uspto-grants-1985_02
Patent number
US04500708

Reaction notes

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