Sodium Carbonate → HCID 14880468, compound

HRID 1533980Notes

Reaction equation

HRID 1533980 reaction equation
C[O:2][C:3]1[CH:29]=[CH:28][CH:27]=[CH:26][C:4]=1[C:5]([C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][N:11]2[S:16]([C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1)(=[O:18])=[O:17])=[O:6].Cl.N1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>>[OH:2][C:3]1[CH:29]=[CH:28][CH:27]=[CH:26][C:4]=1[C:5]([C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][N:11]2[S:16]([C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1)(=[O:18])=[O:17])=[O:6]

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 10176127Pyridinium chlorideHCID 14880467HCID 14880467, compound

Product 1

HCID 14880468HCID 14880468, compoundYield 96%

Conditions

Temperature
180 °C

Procedure

A mixture of 85 g of the product of Step B and 600 g of pyridine hydrochloride was heated at 180° C. for 4 hours and the mixture was cooled to 80° C. 700 ml of a saturated solution of sodium carbonate were added followed by extraction with ethyl acetate. The extracts were washed twice with 300 ml of N hydrochloric acid and then with water, dried and evaporated to dryness under reduced pressure. The 100.3 g of residue were chromatographed on silica (eluant: methylene chloride - hexane (8-2)) to obtain 78.8 g of the expected product which was used as is for the following step and melted at 110° C.

Workup

  1. temperaturethe mixture was cooled to 80° C
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe extracts were washed twice with 300 ml of N hydrochloric acid
  4. dry with materialwith water, dried
  5. customevaporated to dryness under reduced pressure
  6. customThe 100.3 g of residue were chromatographed on silica (eluant: methylene chloride - hexane (8-2))

Sources & evidence

ORD record
ord-281958df41084061a6dc296f8f794619
Source dataset
uspto-grants-1992_02
Patent number
US05086070

Reaction notes

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