Ethyl Acetate → N-[2-[[[5-(Methylamino)methyl-2-furanyl]methyl]thio]ethyl]-N'-methylurea

HRID 127323Notes

Reaction equation

HRID 127323 reaction equation
[SH:1][CH2:2][CH2:3][NH:4][C:5]([NH:7][CH3:8])=[O:6].[CH3:9][NH:10][CH2:11][C:12]1[O:16][C:15]([CH2:17]O)=[CH:14][CH:13]=1.C(OCC)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>Cl.O>[CH3:9][NH:10][CH2:11][C:12]1[O:16][C:15]([CH2:17][S:1][CH2:2][CH2:3][NH:4][C:5]([NH:7][CH3:8])=[O:6])=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 533907Urea, N-(2-mercaptoethyl)-N'-methyl-HCID 146717475-[(Methylamino)methyl]-2-furanmethanol

Product 1

HCID 23452126N-[2-[[[5-(Methylamino)methyl-2-furanyl]methyl]thio]ethyl]-N'-methylureaYield 11.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

To a stirred solution of N-[2-mercaptoethyl]-N'-methylurea (2.0 g) in concentrated hydrochloric acid at 0° was added dropwise a solution of 5-(methylamino)methyl-2-furanmethanol (2.0 g) in water (3 ml). After 24 hr, ethyl acetate (100 ml) and excess anhydrous sodium carbonate were added. The suspension was filtered, the filtrate evaporated to dryness and the oily residue column chromatographed (silica/methanol:0.88 ammonia 79:1). The relevant eluate was evaporated to dryness to give an oil identical to product of Example 4 (0.42 g).

Workup

  1. filtrationThe suspension was filtered
  2. customthe filtrate evaporated to dryness
  3. customthe oily residue column chromatographed (silica/methanol:0.88 ammonia 79:1)
  4. customThe relevant eluate was evaporated to dryness

Sources & evidence

ORD record
ord-a8f71213a5ba46e99721705011c3fe7c
Source dataset
uspto-grants-1981_03
Patent number
US04255440

Reaction notes

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