Hexane → HCID 53816172, compound

HRID 615703Notes

Reaction equation

HRID 615703 reaction equation
[CH3:1][C:2]([CH3:10])([CH3:9])[CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7].S(Cl)(Cl)=O.CCCCCC.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[C:29](=[O:44])[N:30]([CH2:42]O)[CH:31]=[C:32]3[C:37]=2[NH:36][C:35]2[CH:38]=[CH:39][CH:40]=[CH:41][C:34]=2[S:33]3)=[CH:24][CH:23]=1>N1C=CC=CC=1>[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([C:28]2[C:29](=[O:44])[N:30]([CH2:42][O:7][C:6](=[O:8])[CH2:5][CH2:4][CH2:3][C:2]([CH3:10])([CH3:9])[CH3:1])[CH:31]=[C:32]3[C:37]=2[NH:36][C:35]2[CH:38]=[CH:39][CH:40]=[CH:41][C:34]=2[S:33]3)=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 24386Thionyl ChlorideHCID 30151835,5-Dimethylhexanoic acidHCID 20426898HCID 20426898, compound

Product 1

HCID 53816172HCID 53816172, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 3.0 g. of 5,5-dimethylhexanoic acid (23.0 mmol.) and 2.5 ml. of thionyl chloride (34.3 mmol.) was allowed to stand at room temperature for 16 hours. Upon addition of 20 ml. of Skellysolve B, the resulting solution was refluxed for 1 hour, then the solvent was removed in vacuo. The remaining residue was azeotroped twice with Skellysolve B to yield a pale yellow liquid which was added dropwise to a suspension of 3.0 g. of 4-(4-chlorophenyl)-2-(hydroxymethyl)-5H-pyrido[3,4-b][1,4]benzothiazin-3(2H)-one (8.4 mmol.) in 30 ml. of cold pyridine. After stirring in an ice-bath for 35 minutes, the reaction mixture was poured onto ice-water resulting in the formation of a solid product which was filtered, washed with water, and purified using flash chromotography on silica gel, using a mixture of 5% ethyl acetate: 95% methylene chloride as the eluent. Fractions containing product were combined and triturated with diethyl ether to yield 4 -(4-chlorophenyl)-2-[(5,5-dimethyl-1-oxohexyloxy)methyl]-5H-pyrido[3,4-b][1,4]-benzothiazin-3(2H)-one as a yellow solid (2.4 g; 59% yield) having the structural formula, ##STR15## a melting point in the range of 143°-145° C. and the following elemental analysis:

Workup

  1. additionA mixture of 3.0 g
  2. additionUpon addition of 20 ml
  3. customthe solvent was removed in vacuo
  4. customThe remaining residue was azeotroped twice with Skellysolve B
  5. customto yield a pale yellow liquid which
  6. additionwas added dropwise to a suspension of 3.0 g
  7. additionthe reaction mixture was poured onto ice-water resulting in the formation of a solid product which
  8. filtrationwas filtered
  9. washwashed with water
  10. custompurified
  11. additiona mixture of 5% ethyl acetate
  12. additionFractions containing product
  13. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-a60e8086d30644389ae5d95cf0313171
Source dataset
uspto-grants-1985_02
Patent number
US04500708

Reaction notes

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