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

HRID 65758Notes

Reaction equation

HRID 65758 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-af0dee2aa9d94994b8236e3014e0c9cf
Source dataset
uspto-grants-1978_12
Patent number
US04128658

Reaction notes

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