Diisopropylethylamine → HCID 67624332, compound

HRID 362420Notes

Reaction equation

HRID 362420 reaction equation
[Cl:1][C:2]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:3]=1[C:4]([NH:6][C:7]1[C:15]([CH3:16])=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][C:8]=1[CH3:17])=[O:5].C([N:26]([CH2:30][CH3:31])[CH:27]([CH3:29])[CH3:28])(C)C>S(Cl)(Cl)=O.C(Cl)Cl>[CH:8]1[C:28]2[CH2:19][C:18]3[CH:3]=[CH:2][CH:21]=[CH:20][C:31]=3[CH2:30][N:26]([C:11]([C:10]3[CH:14]=[C:15]([CH3:16])[C:7]([NH:6][C:4](=[O:5])[C:3]4[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:2]=4[Cl:1])=[C:8]([CH3:17])[CH:9]=3)=[O:13])[C:27]=2[CH:29]=[CH:15][CH:7]=1

Participants

5

Reactant 2

HCID 81531DiisopropylethylamineHCID 53968745HCID 53968745, compound

Product 1

HCID 67624332HCID 67624332, compoundYield 146.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A mixture of 1.69 g of 4-[(2,4-dichlorobenzoyl)amino]-3,5-dimethylbenzoic acid in 2.0 ml of thionyl chloride is heated on a steam bath under argon for 1 hour. The volatiles are evaporated and the residue evaporated in vacuo from toluene to give a residue. A solution of the residue in 25 ml of methylene chloride is treated with 0.75 g of N,N-diisopropylethylamine and 0.98 g of 10,11-dihydro-5H-dibenz[b,e]azepine is stirred at room temperature for 18 hours. The reaction mixture is washed with saturated NaHCO3, dried (Na2SO4) and passed through a pad of hydrous magnesium silicate. The filtrate is evaporated to a glass which is dissolved in methylene chloride dried (Na2SO4) and passed through a short pad of hydrous magnesium silicate. The filtrate is evaporated to give 1.89 g of the desired product as an amorphorous solid.

Workup

  1. temperatureis heated on a steam bath under argon for 1 hour
  2. customThe volatiles are evaporated
  3. customthe residue evaporated in vacuo from toluene
  4. customto give a residue
  5. washThe reaction mixture is washed with saturated NaHCO3
  6. dry with materialdried (Na2SO4)
  7. customThe filtrate is evaporated to a glass which
  8. dissolutionis dissolved in methylene chloride
  9. dry with materialdried (Na2SO4)
  10. customThe filtrate is evaporated

Sources & evidence

ORD record
ord-e5d5f5c9bf6f445d85149661b6d74464
Source dataset
uspto-grants-1999_02
Patent number
US05869483

Reaction notes

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