Sodium Chloride → HCID 18916436, compound

HRID 1290636Notes

Reaction equation

HRID 1290636 reaction equation
Cl[C:2]1[S:3][C:4]2[C:10]([NH:11][C:12](=[O:16])[O:13][CH2:14][CH3:15])=[C:9]([F:17])[CH:8]=[C:7]([Cl:18])[C:5]=2[N:6]=1.[NH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.[Cl-].[NH4+].[Cl-].[Na+]>O1CCCC1>[N:19]1([C:2]2[S:3][C:4]3[C:10]([NH:11][C:12](=[O:16])[O:13][CH2:14][CH3:15])=[C:9]([F:17])[CH:8]=[C:7]([Cl:18])[C:5]=3[N:6]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8082PiperidineHCID 25517Ammonium ChlorideHCID 18916442HCID 18916442, compound

Product 1

HCID 18916436HCID 18916436, compoundYield 74.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere a solution of 3.0 grams (9.7 mmole) of ethyl N-(2,4-dichloro-6-fluorobenzothiazol-7-yl)carbamate in 75 mL of tetrahydrofuran was stirred, and 1.7 grams (20 mmole) of piperidine was added. Upon completion of the addition the reaction mixture was stirred for 1.5 hours at ambient temperature. The reaction mixture was then poured into a mixture of 75 mL of aqueous 10% ammonium chloride and 75 mL of an aqueous saturated sodium chloride solution. The resulting mixture was extracted with three 75 mL portions of ethyl acetate. The combined extracts were washed with two 50 mL portions of an aqueous saturated sodium chloride solution. The organic layer was dried with sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure, yielding a brown solid, which was purified by column chromatography on silica gel. Elution was accomplished with 2:1 heptane:ethyl acetate. The product-containing fractions were combined and concentrated, yielding 2.6 grams of ethyl N-[2-(1-piperidinyl)-4-chloro-6-fluorobenzothiazol-7-yl]carbamate. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of the addition the reaction mixture
  2. extractionThe resulting mixture was extracted with three 75 mL portions of ethyl acetate
  3. washThe combined extracts were washed with two 50 mL portions of an aqueous saturated sodium chloride solution
  4. dry with materialThe organic layer was dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customyielding a brown solid, which
  8. customwas purified by column chromatography on silica gel
  9. washElution
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-17bde3808ed74ade96a8caefab14dcc5
Source dataset
uspto-grants-1998_05
Patent number
US05753595

Reaction notes

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