Cesium carbonate → HCID 13588531, compound

HRID 1031067Notes

Reaction equation

HRID 1031067 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].NC1C=CC(S)=CC=1.[C:15]([O:19][C:20]([NH:22][CH:23]([C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:24][C:25](=[CH2:41])[CH2:26][C:27]([NH:38][CH:39]=[O:40])(C(OCC)=O)[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:21])([CH3:18])([CH3:17])[CH3:16]>CN(C)C=O>[C:15]([O:19][C:20]([NH:22][CH:23]([C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:24][C:25](=[CH2:41])[CH2:26][CH:27]([NH:38][CH:39]=[O:40])[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:21])([CH3:18])([CH3:16])[CH3:17]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 145104-AminothiophenolHCID 13588530HCID 13588530, compound

Product 1

HCID 13588531HCID 13588531, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

2.21 g of cesium carbonate and 9.42 g of p-amino-thiophenol were added all at once to a solution of 17.25 g of the product of Step E in 250 ml of dimethylformamide and the mixture was heated at 85° C. for 3 hours and was then returned to room temperature. The solution was filtered and the filtrate was evaporated to dryness under reduced pressure. The oil residue was taken up in 300 ml of chloromethane and the solution was washed with hydrochloric acid and then with a saturated aqueous sodium bicarbonate solution. The oil was purified by HPLC and elution with a 6-4 cyclohexane-ethyl acetate mixture yielded the expected product.

Workup

  1. customwas then returned to room temperature
  2. filtrationThe solution was filtered
  3. customthe filtrate was evaporated to dryness under reduced pressure
  4. washthe solution was washed with hydrochloric acid
  5. customThe oil was purified by HPLC and elution with a 6-4 cyclohexane-ethyl acetate mixture

Sources & evidence

ORD record
ord-d8c03e2f101d469d81e0e4c0bf5d657a
Source dataset
uspto-grants-1992_04
Patent number
US05108990

Reaction notes

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