Palmitoyl chloride → HCID 20426911, compound

HRID 615705Notes

Reaction equation

HRID 615705 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.[C:25](Cl)(=[O:41])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]>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:25](=[O:41])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[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 8206Palmitoyl chlorideHCID 20426898HCID 20426898, compound

Product 1

HCID 20426911HCID 20426911, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 3.0 g. of 4-(4-chlorophenyl)-2-(hydroxymethyl)-5H-pyrido[3,4-b][1,4]benzothiazin-3(2H)-one (8.4 mmol.) suspended in 30 ml. of pyridine at 0° C. was added dropwise 2.5 ml. of hexadecanoyl chloride (10.9 mmol.). After stirring for 45 minutes, the mixture was poured onto ice-water and allowed to stand for 16 hours at room temperature, resulting in the formation of a yellow precipitate. The precipitate was collected, washed with water and air-dried, then purified using flash chromatography on silica gel, using a mixture of 5% ethyl acetate: 95% methylene chloride as the eluent. Fractions containing the product were combined, and the solvent was removed in vacuo. The residue was triturated with diethyl ether to yield 4-(4-chlorophenyl)-2-[(1-oxohexadecyloxy)methyl]-5H-pyrido[3,4-b][1,4]benzothiazin-3(2H)-one as a light yellow solid (1.69 g; 34% yield) having the structural formula, ##STR18## a melting point in the range of 89°-92° 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. customresulting in the formation of a yellow precipitate
  4. customThe precipitate was collected
  5. washwashed with water
  6. customair-dried
  7. custompurified
  8. additiona mixture of 5% ethyl acetate
  9. additionFractions containing the product
  10. customthe solvent was removed in vacuo
  11. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-9b455b3b7f244647a2bc5c466877d153
Source dataset
uspto-grants-1985_02
Patent number
US04500708

Reaction notes

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