Hydrochloric Acid → HCID 21712789, compound

HRID 650598Notes

Reaction equation

HRID 650598 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[CH2:12][S:11][C:10]2[S:15][C:16]([C:18](=O)[NH2:19])=[CH:17][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.C(OCC)(=O)C.Cl>N1C=CC=CC=1.O>[CH2:1]([N:8]1[C:13](=[O:14])[CH2:12][S:11][C:10]2[S:15][C:16]([C:18]#[N:19])=[CH:17][C:9]1=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 21712752HCID 21712752, compound

Product 1

HCID 21712789HCID 21712789, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A mixture of 1-benzyl-6-carbamoyl-2,3-dihydro-2-oxo-1H-thieno[2,3-b][1,4]thiazine (0.18 g) and p-toluenesulfonyl chloride (0.17 g) in pyridine (5 ml) was stirred for 24 hours at room temperature. The reaction mixture was poured into a mixture of ethyl acetate and water, and adjusted to pH 1.5 with concentrated hydrochloric acid. The organic layer was successively washed with water and brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was purified by column chromatography on silica gel eluting with chloroform. The fractions containing the object compound were collected and evaporated in vacuo to give 1-benzyl-6-cyano-2,3-dihydro-2-oxo-1H-thieno[2,3-b][1,4]thiazine (0.11 g)

Workup

  1. washThe organic layer was successively washed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was purified by column chromatography on silica gel eluting with chloroform
  5. additionThe fractions containing the object compound
  6. customwere collected
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-6f67fc876eb3496f938928c0e1928791
Source dataset
uspto-grants-2001_08
Patent number
US06274619B1

Reaction notes

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