Methanol → HCID 178485720, compound

HRID 482261Notes

Reaction equation

HRID 482261 reaction equation
Br.[C:2]([N:5]1[CH2:9][C:8]([CH3:11])([CH3:10])[NH:7][C:6]1=[O:12])(=[NH:4])[NH2:3].C[O-].[Na+].CO.[CH3:18][N:19]([C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[CH:30]=1)[C:20](=[O:28])[C:21]([C:26]#[N:27])=[CH:22]OCC>C(O)CC>[C:26]([C:21]([C:20](=[O:28])[N:19]([CH3:18])[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[CH:30]=1)=[CH:22][NH:4][C:2](=[NH:3])[N:5]1[CH2:9][C:8]([CH3:10])([CH3:11])[NH:7][C:6]1=[O:12])#[N:27]

Participants

6

Reactant 4

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 190638771-Amidino-4,4-dimethyl-2-oxoimidazolidine hydrobromideHCID 536402872-cyano-3-ethoxyacrylic acid N-methyl-N-(3-trifluoromethylphenyl)amide

Product 1

HCID 178485720HCID 178485720, compoundYield 55.7%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

7.12 g (30 mmol) of 1-amidino-4,4-dimethyl-2-oxoimidazolidine hydrobromide were added to a mixture of 70 ml of 1-propanol and 5.5 ml of a 30% strength solution of sodium methylate in methanol (=30 mmol) at room temperature, and the mixture was stirred at room temperature for 20 min. Subsequently, at 20° C., 8.95 g (30 mmol) of 2-cyano-3-ethoxyacrylic acid N-methyl-N-(3-trifluoromethylphenyl)amide were added, and the mixture was stirred at 20° C. for 30 min and at 20°-25° C. for 1.5 hours. The solid which had separated out was then filtered off with suction, washed with 1-propanol and with water and dried as described in Example 1. The original filtrate was worked up as in Example 1. 6.82 g (=55.7% yield) of, according to TLC, virtually pure compound IV were obtained.

Workup

  1. stirringthe mixture was stirred at 20° C. for 30 min and at 20°-25° C. for 1.5 hours
  2. customThe solid which had separated out
  3. filtrationwas then filtered off with suction
  4. washwashed with 1-propanol and with water
  5. customdried

Sources & evidence

ORD record
ord-f77976bb8ca3458e9b9f43e7d21b90e1
Source dataset
uspto-grants-1998_08
Patent number
US05795899

Reaction notes

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