Isopropyl isocyanate → 2-[[[5-(dimethylamino)methyl-2-furanyl]methyl]thio]ethyl-N'-(1-methylethyl)urea

HRID 127316Notes

Reaction equation

HRID 127316 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[O:9][C:8]([CH2:10][S:11][CH2:12][CH2:13][NH2:14])=[CH:7][CH:6]=1)[CH3:3].[CH:15]([N:18]=[C:19]=[O:20])([CH3:17])[CH3:16]>C(#N)C>[CH3:3][N:2]([CH2:4][C:5]1[O:9][C:8]([CH2:10][S:11][CH2:12][CH2:13][NH:14][C:19]([NH:18][CH:15]([CH3:17])[CH3:16])=[O:20])=[CH:7][CH:6]=1)[CH3:1]

Participants

4

Reactant 2

HCID 61277Isopropyl isocyanateHCID 1622035-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamine

Product 1

HCID 234521442-[[[5-(dimethylamino)methyl-2-furanyl]methyl]thio]ethyl-N'-(1-methylethyl)ureaYield 93.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-[[[5-(Dimethylamino)methyl-2-furanyl]methyl]thio]ethanamine (2.14 g) and isopropylisocyanate (0.89 g) were dissolved in acetonitrile and allowed to stand overnight. Solvents were removed and the residue recrystallised from methanol:ether to give N-[2-[[[5-(dimethylamino)methyl-2-furanyl]methyl]thio]ethyl]-N'-(1-methylethyl)urea as crystals m.p. 65°-67° (2.8 g).

Workup

  1. customSolvents were removed
  2. customthe residue recrystallised from methanol

Sources & evidence

ORD record
ord-9b98602efc15448c9f84f1953b3bbeef
Source dataset
uspto-grants-1981_03
Patent number
US04255440

Reaction notes

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