4-Chloroaniline → HCID 66883105, compound

HRID 1784034Notes

Reaction equation

HRID 1784034 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:13][C:12](=[CH2:14])[CH2:11][CH:10]1[C:15]([OH:17])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].OC1C2N=NNC=2C=CC=1.Cl.CN(C)CCCN=C=NCC.[Cl:40][C:41]1[CH:47]=[CH:46][C:44]([NH2:45])=[CH:43][CH:42]=1>C1COCC1.CCN(CC)CC>[C:1]([O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:13][C:12](=[CH2:14])[CH2:11][CH:10]1[C:15](=[O:17])[NH:45][C:44]1[CH:46]=[CH:47][C:41]([Cl:40])=[CH:42][CH:43]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 78124-ChloroanilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 53403819HCID 53403819, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 66883105HCID 66883105, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

A stirred solution of 1.085 g of 35b in 10 ml of THF was treated subsequently with 1.25 ml of NEt3, 0.69 g hydroxybenzotriazole, 1.21 g of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride and 0.63 g of 4-chloroaniline and stirring was continued at 22° C. for 16 h. The mixture was evaporated and the residue partitioned between CH2Cl2 and 1 N HCl. The separated organic layer consisting of a white suspension was filtered and the residue dried to give 1.01 g (64%) of the title compound 35c. MS: 351.4 (M+H)+.

Workup

  1. customThe mixture was evaporated
  2. customthe residue partitioned between CH2Cl2 and 1 N HCl
  3. filtrationwas filtered
  4. customthe residue dried

Sources & evidence

ORD record
ord-42fa57afbabc4cbc93c9f7ca931f91b1
Source dataset
uspto-grants-2009_03
Patent number
US07501413B2

Reaction notes

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