Methylamine → Ranisen

HRID 1379894Notes

Reaction equation

HRID 1379894 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]>C(#N)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

5

Reactant 3

HCID 6329MethylamineHCID 38355832-Nitromethylene-thiazolidineHCID 129547925-Dimethylaminomethylfurfuryl chloride hydrochloride

Product 1

HCID 5039Ranisen

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

Combine 2-nitromethylene-thiazolidine (146 g, 1.0 mol) and acetonitrile (250 mL). Heat to 40° C. Add methylamine (90 g). After 30 minutes, cool to about -10° C. Add a solution of 5-[(dimethylamino)methyl]-2-(chloromethyl)-furan hydrochloride as obtained in Example 3.1, maintained at 50° C. to 60° C. to prevent crystallization (about 322 g of solution over 3 hours). Add methylamine (120 g). Warm to 40° C. while adding methylamine (65 g). After 30 minutes, cool to 0° C. Add the remainder of the solution of 5-[(dimethylamino)methyl]-2-(chloromethyl)-furan hydrochloride. After the addition is complete, evaporate in vacuo to give a residue. Partition the residue between methyl isobutyl ketone and aqueous 10% potassium carbonate solution. Separate the layers and extract the aqueous layer with methyl isobutyl ketone. Combine the organic layers extract with water. Evaporate the organic layer in vacuo to give a residue. Recrystallize the residue from methyl isobutyl ketone to give the title compound.

Workup

  1. temperaturecool to about -10° C
  2. customas obtained in Example 3.1
  3. temperaturemaintained at 50° C. to 60° C.
  4. customcrystallization (about 322 g of solution over 3 hours)
  5. temperatureWarm to 40° C.
  6. additionwhile adding methylamine (65 g)
  7. waitAfter 30 minutes
  8. temperaturecool to 0° C
  9. additionAdd the remainder of the solution of 5-[(dimethylamino)methyl]-2-(chloromethyl)-furan hydrochloride
  10. additionAfter the addition
  11. customevaporate in vacuo
  12. customto give a residue
  13. customPartition the residue between methyl isobutyl ketone and aqueous 10% potassium carbonate solution
  14. customSeparate the layers
  15. extractionextract the aqueous layer with methyl isobutyl ketone
  16. extractionextract with water
  17. customEvaporate the organic layer in vacuo
  18. customto give a residue
  19. customRecrystallize the residue from methyl isobutyl ketone

Sources & evidence

ORD record
ord-9f5893ab230642b493b04b8ccbfc2e5c
Source dataset
uspto-grants-1997_09
Patent number
US05672724

Reaction notes

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