Palmitoyl chloride → 7-chloro-4-(4-chlorophenyl)-2-[(1-oxohexadecyloxy)methyl]-5H-pyrido[3,4-b][1,4]benzothiazin-3(2H)-one

HRID 615708Notes

Reaction equation

HRID 615708 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:10][C:9]3=[CH:11][N:12]([CH2:23][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:25]=1.[C:26](Cl)(=[O:42])[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][CH2:40][CH3:41]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:10][C:9]3=[CH:11][N:12]([CH2:23][O:24][C:26](=[O:42])[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][CH2:40][CH3:41])[C:13](=[O:22])[C:14]([C:15]4[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=4)=[C:8]3[NH:7][C:6]=2[CH:25]=1

Participants

4

Reactant 2

HCID 8206Palmitoyl chlorideHCID 204269037-chloro-4-(4-chlorophenyl)-2-(hydroxymethyl)-5H-pyrido[3,4-b][1,4]benzothiazin-3(2H)-one

Product 1

HCID 204269057-chloro-4-(4-chlorophenyl)-2-[(1-oxohexadecyloxy)methyl]-5H-pyrido[3,4-b][1,4]benzothiazin-3(2H)-oneYield 78%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 1.0 g. of 7-chloro-4-(4-chlorophenyl)-2-(hydroxymethyl)-5H-pyrido[3,4-b][1,4]benzothiazin-3(2H)-one (2.6 mmol.) in 15 ml. of pyridine at 0° C. was added dropwise 0.9 ml. of hexadecanoyl chloride (3.9 mmol.). After stirring for 35 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, employing a mixture of 2% ethyl acetate: 98% methylene chloride as the eluent. Fractions containing the product were combined and triturated with ether to yield 7-chloro-4-(4-chlorophenyl)-2-[(1-oxohexadecyloxy)methyl]-5H-pyrido[3,4-b][1,4]benzothiazin-3(2H)-one as a pale yellow crystalline solid (1.25 g; 78% yield) having the structural formula, ##STR21## a melting point in the range of 120°-122° 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 2% ethyl acetate
  9. additionFractions containing the product
  10. customtriturated with ether

Sources & evidence

ORD record
ord-16a480bb4002469099821fd17033d1e9
Source dataset
uspto-grants-1985_02
Patent number
US04500708

Reaction notes

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