Sulfuric Acid → HCID 19737996, compound

HRID 2255500Notes

Reaction equation

HRID 2255500 reaction equation
S(=O)(=O)(O)[OH:2].CO[CH:8]1[C:13]2[CH:14]=[C:15]([S:17]([NH2:20])(=[O:19])=[O:18])[S:16][C:12]=2[S:11](=[O:22])(=[O:21])[N:10]([CH3:23])[CH2:9]1.[C:24](#[N:26])[CH3:25]>>[C:24]([NH:26][CH:8]1[C:13]2[CH:14]=[C:15]([S:17]([NH2:20])(=[O:18])=[O:19])[S:16][C:12]=2[S:11](=[O:21])(=[O:22])[N:10]([CH3:23])[CH2:9]1)(=[O:2])[CH3:25]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 18357855HCID 18357855, compound

Product 1

HCID 19737996HCID 19737996, compound

Procedure

To sulfuric acid (5.0 g) cooled to 0° C. was added the product from Step E (1.10 g, 3.81 mmol) dissolved in acetonitrile (35 mL) dropwise over 10 min. The mixture was stirred at ambient temperature for 2.5 days and quenched by the addition of ice and ammonium hydroxide to adjust the pH to 10. The acetonitrile was evaporated and the white precipitate was filtered and dried to give 0.41 g of the desired product. The filtrate was extracted with ethyl acetate. Evaporation to dryness gave an additional 0.33 g of the desired product (total yield 57%). Crystallization from methanol-methylene chloride gave colorless crystals: mp 252°-253° C.

Workup

  1. customquenched by the addition of ice and ammonium hydroxide
  2. customThe acetonitrile was evaporated
  3. filtrationthe white precipitate was filtered
  4. customdried

Sources & evidence

ORD record
ord-54790b850f3549bbb7dbd2c4327e3a1c
Source dataset
uspto-grants-1993_08
Patent number
US05240923

Reaction notes

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