Chloride → HCID 20426906, compound

HRID 615704Notes

Reaction equation

HRID 615704 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:24])[N:10]([CH2:22][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:4][CH:3]=1.[Cl-]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:24])[N:10]([CH2:22][O:23][C:9](=[O:24])[CH2:8][CH:5]([CH3:6])[CH3:4])[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

Participants

4

Reactant 2

HCID 312ChlorideHCID 20426898HCID 20426898, compound

Product 1

HCID 20426906HCID 20426906, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 2.5 g. of 4-(4-chlorophenyl)-2-(hydroxymethyl)-5H-pyrido[3,4-b][1,4]benzothiazin-3(2H)-one (7.0 mmol.) in 25 ml. of pyridine at 0° C. was added 2.5 ml. of isovalery chloride (20.5 mmol.). After stirring for 35 minutes, the mixture was poured onto ice-water and allowed to stand for 16 hours at room temperature. The crude product which formed as an orange precipitate was collected, washed with water, air-dried, and purified using flash chromotography on silica gel, using a mixture of 5% ethyl acetate: 95% methylene chloride as the eluent. Fractions containing the product were combined and triturated with ether to yield 4-(4-chlorophenyl)-2-[(3-methyl-1-oxobutoxy)methyl]-5H-pyrido-[3,4-b][1,4]benzothiazin-3(2H)-one as a yellow solid (1.1 g; 36% yield) having the structural formula, ##STR16## a melting point in the range of 163°-171° C. and the following elemental analysis:

Workup

  1. additionthe mixture was poured onto ice-water
  2. waitto stand for 16 hours at room temperature
  3. customThe crude product which formed as an orange precipitate
  4. customwas collected
  5. washwashed with water
  6. customair-dried
  7. custompurified
  8. additiona mixture of 5% ethyl acetate
  9. additionFractions containing the product
  10. customtriturated with ether

Sources & evidence

ORD record
ord-e4bd436ba93846a6922a824d8aad5376
Source dataset
uspto-grants-1985_02
Patent number
US04500708

Reaction notes

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