Sodium Carbonate → HCID 86673695, compound

HRID 1616901Notes

Reaction equation

HRID 1616901 reaction equation
[CH2:1]1[CH:6]2[O:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[CH:5]2[CH2:4][CH2:3][N:2]1[C:14](=[O:16])[CH3:15].S(Cl)(Cl)=O.[Cl:21][S:22](O)(=[O:24])=[O:23].C(=O)([O-])[O-].[Na+].[Na+]>>[C:14]([N:2]1[CH2:3][CH2:4][CH:5]2[C:9]3[CH:10]=[C:11]([S:22]([Cl:21])(=[O:24])=[O:23])[CH:12]=[CH:13][C:8]=3[O:7][CH:6]2[CH2:1]1)(=[O:16])[CH3:15]

Participants

5

Reactant 4

HCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 24638Chlorosulfonic acidHCID 67324329HCID 67324329, compound

Product 1

HCID 86673695HCID 86673695, compound

Conditions

Temperature
0 °C

Procedure

To a solution of 1-(3,4,4a,9a-tetrahydro-1H-benzo[4,5]furo[2,3-c]pyridin-2-yl)-ethanone (825 mg, 3.8 mmol) and thionyl chloride at 0° C., was added dropwise chlorosulfonic acid (1.25 g). The reaction mixture was stirred for 5 min at 0° C., for 2 h at r.t. and poured tehn into ice/H2O (75 g). The solution was brought to pH 7 by adding sodium carbonate and extracted with 75 mL ethyl acetate (2×). The combined organic layers were washed with H2O (2×), separated, and the solvent was evaporated. The resulting sulfonyl chloride was used in the next reaction step without further purification.

Workup

  1. additionpoured
  2. extractionextracted with 75 mL ethyl acetate (2×)
  3. washThe combined organic layers were washed with H2O (2×)
  4. customseparated
  5. customthe solvent was evaporated
  6. customThe resulting sulfonyl chloride was used in the next reaction step without further purification

Sources & evidence

ORD record
ord-a73dc595d6334d1692372ef72cca3b8f
Source dataset
uspto-grants-2014_07
Patent number
US08765779B2

Reaction notes

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