Sodium Carbonate → 3-propionylamino-N-heptylaniline

HRID 485475Notes

Reaction equation

HRID 485475 reaction equation
[C:1]([NH:5][C:6]1[CH:7]=[C:8]([CH:10]=[CH:11][CH:12]=1)[NH2:9])(=[O:4])[CH2:2][CH3:3].[C:13]1([CH3:30])[CH:18]=[CH:17][C:16](S(OCCCCCCC)(=O)=O)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCO>[C:1]([NH:5][C:6]1[CH:7]=[C:8]([CH:10]=[CH:11][CH:12]=1)[NH:9][CH2:30][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])(=[O:4])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 89953N-(3-Aminophenyl)propanamideHCID 599295Heptyl p-toluenesulfonate

Product 1

HCID 202705503-propionylamino-N-heptylaniline

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

3-Propionylaminoaniline (16.4 parts) was reacted with n-heptyl p-toluenesulfonate (27 parts) at 100° C. for 4 hours in methyl cellosolve (200 parts) in the presence of anhydrous sodium carbonate (5.3 parts) to obtain 3-propionylamino-N-heptylaniline. Thereafter, reaction was further continued at 100° to 110° C. for 4 hours with addition of n-amyl p-toluenesulfonate (24.2 parts) and anhydrous sodium carbonate (5.3 parts) to obtain 3-propionylamino-N-n-heptyl-N-n-pentylaniline (coupling component). In the same manner as in Example 1, 2-cyano-4-nitro-6-chloroaniline was diazotized and coupled with the above coupling component to obtain 45.9 parts of a dye (7).

Sources & evidence

ORD record
ord-4833b72accd647319938cc31b3e4d9df
Source dataset
uspto-grants-1985_08
Patent number
US04536569

Reaction notes

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