Aniline → HCID 59637322, compound

HRID 2271414Notes

Reaction equation

HRID 2271414 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][N:8](C)[CH:9]=[O:10].C(N([CH2:17][CH3:18])CC)C.N[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[C:26]([O:29]CC)(=[O:28])C.[CH3:32][CH2:33][CH2:34][CH2:35][CH2:36]C>ClCCl.O>[C:7]1([NH:8][C:9]([C:20]2[CH:25]=[CH:24][C:23]([CH:17]([CH3:18])[C:26]([OH:29])=[O:28])=[CH:22][CH:21]=2)=[O:10])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

8

Reactant 5

HCID 6115AnilineHCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 21226206Ethyl acetate hexane2×

Product 1

HCID 59637322HCID 59637322, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

Step f-g: To a stirred solution of step-e product (2.3 g, 10 mmol) in dichloromethane (23 ml), oxalyl chloride (2.08 g (1.44 ml), 16 mmol, 1.5 eq) followed by catalytic amount of dimethylformamide were added at room temperature. Reaction contents were stirred for 20 minutes at room temperature. Progress of the reaction was monitored by TLC (5% ethyl acetate-hexane, Rf˜0.7). As the reaction not moved completely, reaction contents were heated to 40° C. and stirred for 1 hr at the same temperature. Again TLC was checked and confirmed that the starting material was disappeared. Dichloromethane was distilled off completely under reduced pressure. In another round-bottom flask, TEA (triethylamine) (3.2 g (2.5 ml), 25 mmol, 2.5 eq) was added to a solution of aniline (0.83 g, 9 mmol) in dichloromethane (10 ml) and stirred the contents for 15 minutes at 0° C. Then the above prepared acid chloride was taken in dichloromethane (13 ml) and added dropwise at 0° C. and the overall reaction mixture was allowed to stir for 1 hr at 0° C. Progress of the reaction was monitored by TLC (5% ethyl acetate-hexane, Rf˜0.3). On completion of the reaction, water (10 ml) was added and the layers formed were separated out. Organic layer was dried over sodium sulfate and concentrated under reduced pressure to yield the required product as an off white solid (3 g, 96%).

Workup

  1. additionwere added at room temperature
  2. customReaction contents
  3. customAs the reaction not
  4. customreaction contents
  5. temperaturewere heated to 40° C.
  6. stirringstirred for 1 hr at the same temperature
  7. distillationDichloromethane was distilled off completely under reduced pressure
  8. stirringstirred the contents for 15 minutes at 0° C
  9. additionadded dropwise at 0° C.
  10. stirringto stir for 1 hr at 0° C
  11. additionwas added
  12. customthe layers formed
  13. customwere separated out
  14. dry with materialOrganic layer was dried over sodium sulfate
  15. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c0a8222e3a7d492cbc6f700e39292d77
Source dataset
uspto-grants-2015_09
Patent number
US09120756B2

Reaction notes

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