Dimethylformamide → HCID 136344324, compound

HRID 1400104Notes

Reaction equation

HRID 1400104 reaction equation
[OH:1][NH:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH:16]3[CH2:17][CH2:18][CH:12]2[CH2:13][N:14]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15]3)=[N:9][CH:10]=1)=[NH:4].CN([CH:29]=[O:30])C.ClC(OC)=O>N1C=CC=CC=1>[O:30]=[C:29]1[O:1][N:2]=[C:3]([C:5]2[CH:6]=[CH:7][C:8]([N:11]3[CH:12]4[CH2:18][CH2:17][CH:16]3[CH2:15][N:14]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:13]4)=[N:9][CH:10]=2)[NH:4]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 6586Methyl chloroformateHCID 178451467HCID 178451467, compound

Product 1

HCID 136344324HCID 136344324, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1 g of the compound from step c) is placed in a round-bottomed flask under a stream of nitrogen, and 10 ml of DMF and 0.3 ml of pyridine are added. 0.23 ml of methyl chloroformate is added at 0° C., and the mixture is stirred at room temperature for 3 hours. The resulting mixture is washed with water and extracted with ethyl acetate. The organic phase is dried over Na2SO4, filtered and evaporated under vacuum. 30 ml of toluene are added and the resulting mixture is stirred at reflux for 4 hours. The solvent is evaporated off to give 0.8 g of the title compound.

Workup

  1. additionare added
  2. washThe resulting mixture is washed with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase is dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated under vacuum
  7. addition30 ml of toluene are added
  8. stirringthe resulting mixture is stirred
  9. temperatureat reflux for 4 hours
  10. customThe solvent is evaporated off

Sources & evidence

ORD record
ord-3a331bc8ba624419844fe5ffdbaba0a3
Source dataset
uspto-grants-2014_12
Patent number
US08906924B2

Reaction notes

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