Ethyl Acetate → HCID 21277591, compound

HRID 2291967Notes

Reaction equation

HRID 2291967 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[NH2:12][CH2:13][CH:14]([OH:17])[CH2:15][OH:16].C(OCC)(=O)C>CS(C)=O>[OH:17][CH:14]([CH2:15][OH:16])[CH2:13][NH:12][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 679672,4-DifluoronitrobenzeneHCID 735613-Amino-1,2-propanediol

Product 1

HCID 21277591HCID 21277591, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
23 °C

Procedure

To a stirred solution of 2,4-difluoronitrobenzene (3.18 g., 20 mmole) in DMSO (10 ml) was added portion-wise a solution of 3-amino-1,2-propanediol (3.64 g., 40 mmole) in DMSO (5 ml) in an ice bath. The mixture was stirred at 23° C. for 30 min. and poured into crushed ice. After addition of ethyl acetate, the organic layer was separated, washed with water, dried over sodium sulfate and evaporated under reduced pressure to give the compound (18) (3.6 g., 78%) as a yellow solid.

Workup

  1. additionpoured
  2. custominto crushed ice
  3. customthe organic layer was separated
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-79bc126d26bc4d42b5d48227683b8dc3
Source dataset
uspto-grants-1989_01
Patent number
US04799934

Reaction notes

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