Methyl Isocyanate → Des(N'-Methyl-2-nitro-1,1-ethenediaMino) N'-Methylureido Nizatidine

HRID 850933Notes

Reaction equation

HRID 850933 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11][CH2:12][CH2:13][NH2:14])[N:9]=1)[CH3:3].[CH3:15][N:16]=[C:17]=[O:18]>C(#N)C>[CH3:15][NH:16][C:17]([NH:14][CH2:13][CH2:12][S:11][CH2:10][C:8]1[N:9]=[C:5]([CH2:4][N:2]([CH3:1])[CH3:3])[S:6][CH:7]=1)=[O:18]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 109773182-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazole

Product 1

HCID 13121954Des(N'-Methyl-2-nitro-1,1-ethenediaMino) N'-Methylureido Nizatidine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Following the above reaction sequence, a solution of 0.93 g of 2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethylamine in 10 ml. of anhydrous acetonitrile was prepared. A solution of 0.22 ml. of methyl isocyanate in 5 ml. of anhydrous acetonitrile was added thereto. The reaction was stirred at ambient temperature for about 2.5 hours at which time the solvent was removed by evaporation. The resulting residue slowly crystallized and was recrystallized from cylcohexane to yield about 0.97 g of N-methyl-N'-2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethylurea melting at about 56°-59° C.

Workup

  1. customwas removed by evaporation
  2. customThe resulting residue slowly crystallized
  3. customwas recrystallized from cylcohexane

Sources & evidence

ORD record
ord-4483e5165f5a4b07b1fc147443e8454a
Source dataset
uspto-grants-1983_05
Patent number
US04382090

Reaction notes

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