Sulfuric Acid → HCID 67917571, compound

HRID 1534876Notes

Reaction equation

HRID 1534876 reaction equation
O[CH:2]1[CH2:7][CH:6]([CH2:8][CH2:9][CH3:10])[S:5](=[O:12])(=[O:11])[C:4]2[S:13][C:14]([S:16]([NH2:19])(=[O:18])=[O:17])=[CH:15][C:3]1=2.[OH:20]S(O)(=O)=O.[C:25](#[N:27])[CH3:26]>>[C:25]([NH:27][CH:2]1[CH2:7][CH:6]([CH2:8][CH2:9][CH3:10])[S:5](=[O:12])(=[O:11])[C:4]2[S:13][C:14]([S:16]([NH2:19])(=[O:18])=[O:17])=[CH:15][C:3]1=2)(=[O:20])[CH3:26]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 67917629HCID 67917629, compound

Product 1

HCID 67917571HCID 67917571, compound

Procedure

A suspenison of 6 (47.41 g, 0.146 mol) in acetonitrile (500 ml) was chilled to -10° C. The cold stirring suspension was treated with 95% H2SO4 (165.5 ml, 3.11 mol) at a rate sufficient to maintain the temperature below 0° C. After equilibrating to room temperature overnight, the resulting solution was poured over ice and was stirred for 4.0 hours. The resulting aqueous suspension was partitioned between 1000 ml and 250 ml of ethyl acetate. The aqueous phase was collected, buffered to pH 8, and partitioned with an additional 50 ml of ethyl acetate. All organic phases were combined and washed with 250 ml of saturated aqueous sodium bicarbonate followed by washing with 250 ml of saturated aqueous sodium chloride. The dried (Na2SO4) organic phase was filtered and concentrated to give 55.27 g (quantitative) of 7 as an orange foam.

Workup

  1. temperatureto maintain the temperature below 0° C
  2. additionthe resulting solution was poured over ice
  3. stirringwas stirred for 4.0 hours
  4. customThe resulting aqueous suspension was partitioned between 1000 ml and 250 ml of ethyl acetate
  5. customThe aqueous phase was collected
  6. custompartitioned with an additional 50 ml of ethyl acetate
  7. washwashed with 250 ml of saturated aqueous sodium bicarbonate
  8. washby washing with 250 ml of saturated aqueous sodium chloride
  9. dry with materialThe dried (Na2SO4) organic phase
  10. filtrationwas filtered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-4170be29d13b481fa0a8cf6cc4b7e60a
Source dataset
uspto-grants-1992_02
Patent number
US05091409

Reaction notes

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