Thionyl Chloride → HCID 90370056, compound

HRID 2176031Notes

Reaction equation

HRID 2176031 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:26]=[CH:27][CH:28]=2)[C:11]([NH:13][C:14]2[S:15][C:16]3[CH2:25][CH2:24][CH2:23][CH2:22][C:17]=3[C:18]=2[C:19]([OH:21])=[O:20])=O)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.S(Cl)(Cl)=O>C1(C)C=CC=CC=1>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([C:11]3[O:20][C:19](=[O:21])[C:18]4[C:17]5[CH2:22][CH2:23][CH2:24][CH2:25][C:16]=5[S:15][C:14]=4[N:13]=3)[CH:26]=[CH:27][CH:28]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 90370047HCID 90370047, compound

Product 1

HCID 90370056HCID 90370056, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 22.2 g of 2-{[3-(morpholin-4-ylmethyl)benzoyl]amino}-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylic acid and 230 mL of toluene was heated at 60° C., and 20 mL of thionyl chloride was added thereto, followed by stirring for 1 hour at 60° C. The insoluble material was collected by filtration and washed with toluene. A saturated aqueous sodium hydrogen carbonate solution and ethyl acetate were added to the material collected by filtration, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was washed with ethanol, thereby obtaining 18.9 g of 2-[3-(morpholin-4-ylmethyl)phenyl]-5,6,7,8-tetrahydro-4H-[1]benzothieno[2,3-d][1,3]oxazin-4-one.

Workup

  1. filtrationThe insoluble material was collected by filtration
  2. washwashed with toluene
  3. additionA saturated aqueous sodium hydrogen carbonate solution and ethyl acetate were added to the material
  4. filtrationcollected by filtration
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was removed under reduced pressure
  9. washThe residue was washed with ethanol

Sources & evidence

ORD record
ord-55ef6bd9cd84435a8ce0f92b518dc6a4
Source dataset
uspto-grants-2015_06
Patent number
US09062032B2

Reaction notes

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