Sulfuric Acid → HCID 21837530, compound

HRID 1739802Notes

Reaction equation

HRID 1739802 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([N:11]3[CH2:16][CH2:15][C:14](O)([CH3:17])[CH2:13][CH2:12]3)[C:5]=2[O:4][CH2:3][CH2:2]1.[OH:19]S(O)(=O)=O.[C:24](#[N:26])[CH3:25]>>[C:24]([NH:26][C:14]1([CH3:17])[CH2:15][CH2:16][N:11]([C:10]2[C:5]3[O:4][CH2:3][CH2:2][O:1][C:6]=3[CH:7]=[CH:8][CH:9]=2)[CH2:12][CH2:13]1)(=[O:19])[CH3:25]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 21837536HCID 21837536, compound

Product 1

HCID 21837530HCID 21837530, compound

Procedure

1.03 g (4.1 mmol) of the product of Step 1 are dissolved in 4 ml of acetonitrile. 1 ml of concentrated H2SO4 is added dropwise over a period of 5 minutes while the temperature is maintained below 40° C. The whole is stirred overnight at room temperature and then poured into 50 ml of ice-cold 1N sodium hydroxide solution. The whole is extracted with methylene chloride, washed with water, dried and evaporated to yield 0.85 g of residue, which is purified by flash chromatography (eluants:methylene chloride/ethyl acetate: 50/50, then methylene chloride/methanol: 98/2). 0.54 g of the expected product is obtained.

Workup

  1. temperatureis maintained below 40° C
  2. extractionThe whole is extracted with methylene chloride
  3. washwashed with water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-7cdb1516b2c443968591f66fc96b031c
Source dataset
uspto-grants-1999_10
Patent number
US05968954

Reaction notes

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