Hydrochloric Acid → ethyl 4-[5-[3-methoxy-4-[N,N-bis(1-methylethyl)aminocarbonyl]phenoxy]pentoxy]benzenecarboximidoate monohydrochloride

HRID 376068Notes

Reaction equation

HRID 376068 reaction equation
[CH2:1]([OH:3])[CH3:2].Cl.C(C1C=C[C:10]([O:11]CCCCCOC2C=CC(C([Cl:24])=O)=CC=2OC)=CC=1)#N.[C:31]([C:33]1[CH:62]=[CH:61][C:36]([O:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][O:43][C:44]2[CH:58]=[CH:57][C:47]([C:48]([N:50]([CH:54]([CH3:56])[CH3:55])[CH:51]([CH3:53])[CH3:52])=[O:49])=[CH:46][C:45]=2OC)=[CH:35][CH:34]=1)#[N:32]>C(OCC)(=O)C.CCCCCC>[ClH:24].[CH3:10][O:11][C:46]1[CH:45]=[C:44]([CH:58]=[CH:57][C:47]=1[C:48]([N:50]([CH:54]([CH3:56])[CH3:55])[CH:51]([CH3:52])[CH3:53])=[O:49])[O:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][O:37][C:36]1[CH:61]=[CH:62][C:33]([C:31](=[NH:32])[O:3][CH2:1][CH3:2])=[CH:34][CH:35]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid3×HCID 702EthanolHCID 189916954-[5-(4-cyanophenoxy)pentoxy]-3-methoxy-N,N-bis(1-methylethyl)-benzamideHCID 189917904-[5-(4-Cyanophenoxy)pentoxy]-3-methoxybenzoyl chloride

Product 1

HCID 18991643ethyl 4-[5-[3-methoxy-4-[N,N-bis(1-methylethyl)aminocarbonyl]phenoxy]pentoxy]benzenecarboximidoate monohydrochloride

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
10 °C

Procedure

Ethanol (2B,6.0 L) is cooled in an ice bath to 0° C. and saturated with anhydrous hydrogen chloride over a period of 71/2 hours. The solution is left in the ice bath overnight and the hydrogen chloride addition is continued an additional hour at 0° C. 4-[5-(4-Cyanophenoxy)pentoxy]-3-methoxy-N,N-bis(1-methylethyl)-benzamide (4200 g, 9.57 mole) is added rapidly over 30 minutes and an exotherm raises the reaction mixture temperature to 10° C. Hydrogen chloride addition is continued for 6 hours and the purple solution stirred overnight at 20° C. The reaction mixture is followed by TLC (ethyl acetate/hexane, 2:1) using silica plates. A total of 4-5 days is required for completion of this reaction with periodic resaturation with hydrogen chloride. The thick purple solution is transferred into a 20 gallon reactor and triturated with anhydrous diethyl ether (2×30 L), removing the ether solution after each wash. The reactor is put under vacuum (3 mm Hg) for 0.5 hour to dispel most of the hydrogen chloride leaving ethyl 4-[5-[3-methoxy-4-[N,N-bis(1-methylethyl)aminocarbonyl]phenoxy]pentoxy]benzenecarboximidoate monohydrochloride as a thick purple oil.

Workup

  1. waitis continued an additional hour at 0° C
  2. customThe thick purple solution is transferred into a 20 gallon reactor
  3. customtriturated with anhydrous diethyl ether (2×30 L)
  4. customremoving the ether solution after each wash
  5. waitThe reactor is put under vacuum (3 mm Hg) for 0.5 hour

Sources & evidence

ORD record
ord-f86ec626180f45bead29dfe4cc8b707d
Source dataset
uspto-grants-1996_01
Patent number
US05488160

Reaction notes

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