4-Chloroaniline → HCID 66882720, compound

HRID 1784030Notes

Reaction equation

HRID 1784030 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][C:9](=[CH2:11])[CH2:8][C@H:7]1[C:12]([OH:14])=O)=[O:5])C.OC1C2N=NNC=2C=CC=1.Cl.CN(C)CCCN=C=NCC.[Cl:37][C:38]1[CH:44]=[CH:43][C:41]([NH2:42])=[CH:40][CH:39]=1>CC#N.CCN(CC)CC>[CH3:1][O:3][C:4]([C@@H:6]1[CH2:10][C:9](=[CH2:11])[CH2:8][C@H:7]1[C:12](=[O:14])[NH:42][C:41]1[CH:43]=[CH:44][C:38]([Cl:37])=[CH:39][CH:40]=1)=[O:5]

Participants

7

Reactant 4

HCID 78124-ChloroanilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66882442HCID 66882442, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 66882720HCID 66882720, compoundYield 55.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

The crude mixture containing 1a (16.7 g) was dissolved in 500 ml of CH3CN and treated subsequently with 51 ml of NEt3, 25.0 g hydroxybenzotriazole and 31.3 g of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride and stirring was continued at 22° C. for 30 min. The mixture was treated with 23.1 g of 4-chloroaniline and stirring was continued at 22° C. for 16 h and at 60° C. for 5 h. The mixture was evaporated and the residue partitioned between AcOEt and 0.1 N NaOH. The organic layer was washed with 0.1 N NaOH, 1 N HCl and brine, dried and evaporated to give 13.7 g of the crude title compound 1b.

Workup

  1. stirringstirring
  2. waitwas continued at 22° C. for 16 h and at 60° C. for 5 h
  3. customThe mixture was evaporated
  4. customthe residue partitioned between AcOEt and 0.1 N NaOH
  5. washThe organic layer was washed with 0.1 N NaOH, 1 N HCl and brine
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-874f0f7e20284885950217314592bb1d
Source dataset
uspto-grants-2009_03
Patent number
US07501413B2

Reaction notes

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