Hydrochloric Acid → HCID 58988191, compound

HRID 2194993Notes

Reaction equation

HRID 2194993 reaction equation
C[O-].[Na+].[O:4]=[C:5]1[C:13]2[S:12][C:11]([NH:14][C:15](=[O:17])[CH3:16])=[N:10][C:9]=2[CH2:8][CH2:7][CH2:6]1.[CH:18](OCC)=[O:19].Cl>CN(C)C=O.C1C=CC=CC=1>[CH:18]([CH:6]1[CH2:7][CH2:8][C:9]2[N:10]=[C:11]([NH:14][C:15](=[O:17])[CH3:16])[S:12][C:13]=2[C:5]1=[O:4])=[O:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8025Ethyl formateHCID 597793N-(7-Oxo-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)acetamideHCID 10942334Sodium Methoxide

Product 1

HCID 58988191HCID 58988191, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

20 g (0.37 mol) sodium methoxide are suspended in 50 mL dimethylformamide, a suspension of 21 g (0.1 mol) N-(7-oxo-4,5,6,7-tetrahydro-benzothiazol-2-yl)-acetamide in 100 mL dimethylformamide is added dropwise. The mixture is stirred for 15 minutes, then cooled to 0° C. A mixture of 29.9 mL (0.37 mol) ethyl formate and 60 mL benzene is added dropwise and the reaction mixture is diluted with another 100 mL benzene. A precipitate gradually settles out and stirring is continued at 0° C. for 3.5 hours. The suspension is hydrolysed with 370 mL 1 molar hydrochloric acid, the solid precipitated is suction filtered. The two phases of the mother liquor are separated, the aqueous phase is extracted with dichloromethane. The resulting organic phase is dried and evaporated to dryness. The solid and the residue from the extraction are recrystallised from acetonitrile. Yield: 20 g

Workup

  1. additionis added dropwise
  2. additionis added dropwise
  3. stirringstirring
  4. waitis continued at 0° C. for 3.5 hours
  5. customthe solid precipitated
  6. filtrationfiltered
  7. customThe two phases of the mother liquor are separated
  8. extractionthe aqueous phase is extracted with dichloromethane
  9. customThe resulting organic phase is dried
  10. customevaporated to dryness
  11. extractionThe solid and the residue from the extraction
  12. customare recrystallised from acetonitrile

Sources & evidence

ORD record
ord-9928775d2d9347ebb951bec6a8803dfc
Source dataset
uspto-grants-2012_12
Patent number
US08334378B2

Reaction notes

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