Formaldehyde → HCID 20426898, compound

HRID 615700Notes

Reaction equation

HRID 615700 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:22])[NH:10][CH:11]=[C:12]3[C:17]=2[NH:16][C:15]2[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=2[S:13]3)=[CH:4][CH:3]=1.[OH-:23].[Na+].[CH2:25]=O>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9](=[O:22])[N:10]([CH2:25][OH:23])[CH:11]=[C:12]3[C:17]=2[NH:16][C:15]2[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=2[S:13]3)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 13051480HCID 13051480, compound

Product 1

HCID 20426898HCID 20426898, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 5.0 g. of 4-(4-chlorophenyl)-5H-pyrido[3,4-b][1,4]benzothiazin-3-(2H)-one (15.3 mmol.) in 50 ml. of 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 a solution formed. To the solution was then added 50 ml. of a 36% formaldehyde solution (60.0 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 4-(4-chlorophenyl)-2-(hydroxymethyl)-5H-pyrido[3,4-b][1,4]benzothiazin-3(2H)-one complexed with water (4:1) as a yellow powder (5.15 g.; 93% yield) having the structural formula, ##STR9## a melting point of greater than 300° C. and the following elemental analysis:

Workup

  1. customformed
  2. additionTo the solution was then added 50 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-8369cc3a223b42048d98d97bc7c7c9d8
Source dataset
uspto-grants-1985_02
Patent number
US04500708

Reaction notes

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