Ammonia → HCID 178493640, compound

HRID 2378155Notes

Reaction equation

HRID 2378155 reaction equation
C(O/[CH:4]=[CH:5]/[C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[C:10]=1[O:16][CH3:17])=[O:7])C.OS(O)(=O)=O.N>>[F:15][C:11]1[C:10]([O:16][CH3:17])=[C:9]2[C:14]([CH:4]=[CH:5][C:6]([OH:7])=[N:8]2)=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 59857987HCID 59857987, compound

Product 1

HCID 178493640HCID 178493640, compoundYield 100%

Procedure

A mixture of (E)-N-(3-fluoro-2-methoxyphenyl)-3-ethoxypropenamide (3a) (3.16 g, 13.2 mmol) and 25 mL of concentrated H2SO4 was allowed to stir overnight at room temperature. The solution was poured over ice and concentrated NH3 was added until pH 5 to precipitate out the product. The mixture was filtered, washed and dried to give the product (2.55 g, 87% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) 11.35 (bs, 1H), 7.86 (d, J=9.6Hz, 1H), 7.41 (dd, J=8.8, 5.6 Hz, 1H), 7.08 (dd, J=11.2, 8.8 Hz, 1H), 6.45 (d, J=10 Hz, 1H), 3.87 (s, 3H). 19F NMR (376 MHz, DMSO-d6) −128.88 (dd, J=11.5, 5.5 Hz).

Workup

  1. additionwas added until pH 5
  2. customto precipitate out the product
  3. filtrationThe mixture was filtered
  4. washwashed
  5. customdried

Sources & evidence

ORD record
ord-da5d46ddc19e4c15b048d01317d418db
Source dataset
uspto-grants-2008_12
Patent number
US07470788B2

Reaction notes

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