Formaldehyde → HCID 20426902, compound

HRID 615711Notes

Reaction equation

HRID 615711 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]1[CH:4]=[CH:5][C:6]2[S:11][C:10]3=[CH:12][NH:13][C:14](=[O:23])[C:15]([C:16]4[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=4)=[C:9]3[NH:8][C:7]=2[CH:24]=1.[OH-:27].[Na+].[CH2:29]=O>CN(C)C=O>[F:26][C:2]([F:25])([F:1])[C:3]1[CH:4]=[CH:5][C:6]2[S:11][C:10]3=[CH:12][N:13]([CH2:29][OH:27])[C:14](=[O:23])[C:15]([C:16]4[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=4)=[C:9]3[NH:8][C:7]=2[CH:24]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 20426913HCID 20426913, compound

Product 1

HCID 20426902HCID 20426902, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 1.0 g. of 7-trifluoromethyl-4-(4-chlorophenyl)-5H-pyrido[3,4-b][1,4]benzothiazin-3(2H)-one (2.5 mmol.) in 10 ml. dimethylformamide was added 6.0 ml. of a 5% sodium hydroxide solution (7.5 mmol.), and the resulting suspension was heated on a steam bath until a solution formed. To the solution was then added 10 ml. of a 36% formaldehyde solution (12.0 mmol.), and the resulting reaction mixture was heated until a yellow precipitate formed. The hot reaction mixture was filtered, and the precipitate was washed with water and dried under high vacuum at room temperature to yield 7-trifluoromethyl-4-(4-chlorophenyl)-2-(hydroxymethyl)-5H-pyrido[3,4-b][1,4]benzothiazin-3(2H)-one as a yellow powder (1.0 g.; 94% yield) having the structural formula, ##STR24## a melting point of 204° C. (with decomposition) and the following elemental analysis:

Workup

  1. customformed
  2. additionTo the solution was then added 10 ml
  3. temperaturewas heated until a yellow precipitate
  4. customformed
  5. filtrationThe hot reaction mixture was filtered
  6. washthe precipitate was washed with water
  7. customdried under high vacuum at room temperature

Sources & evidence

ORD record
ord-fc0b0ef3591d48d8b76335ca7e2f3747
Source dataset
uspto-grants-1985_02
Patent number
US04500708

Reaction notes

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