Methylamine → Ranisen

HRID 1379892Notes

Reaction equation

HRID 1379892 reaction equation
[N+:1]([CH:4]=[C:5]1[NH:9][CH2:8][CH2:7][S:6]1)([O-:3])=[O:2].[CH3:10][NH2:11].Cl.[CH3:13][N:14]([CH2:16][C:17]1[O:21][C:20]([CH2:22]Cl)=[CH:19][CH:18]=1)[CH3:15].[OH-].[Na+]>O.C(O)(C)C>[CH3:13][N:14]([CH2:16][C:17]1[O:21][C:20]([CH2:22][S:6][CH2:7][CH2:8][NH:9][C:5]([NH:11][CH3:10])=[CH:4][N+:1]([O-:3])=[O:2])=[CH:19][CH:18]=1)[CH3:15]

Participants

7

Reactant 4

HCID 6329MethylamineHCID 14798Sodium HydroxideHCID 38355832-Nitromethylene-thiazolidineHCID 129547925-Dimethylaminomethylfurfuryl chloride hydrochloride

Product 1

HCID 5039Ranisen

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
40 °C

Procedure

Combine 2-nitromethylene-thiazolidine (10.0 g) and isopropanol (40 mL). Add methylamine (14.7 g). Heat to 40° C. After 5 minutes, add 5-[(dimethylamino)methyl]-2-(chloromethyl)-furan hydrochloride (13.05 g) portionwise over 1.5 hours. After 3 hours, cool to ambient temperature. Add aqueous sodium hydroxide solution (11.6 g, 50% by weight) and water (20 g). Extract repeatedly with methyl isobutyl ketone. Combine the organic layers and evaporate in vacuo to give the title compound.

Workup

  1. waitAfter 3 hours
  2. temperaturecool to ambient temperature
  3. extractionExtract repeatedly with methyl isobutyl ketone
  4. customevaporate in vacuo

Sources & evidence

ORD record
ord-35f4417ac36e4c47bb586671403d36df
Source dataset
uspto-grants-1997_09
Patent number
US05672724

Reaction notes

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