Methyl Isocyanate → 4-(5-Tert-butyl-1,3,4-thiadiazol-2-ylcarbamoylmethyl)-2-(3-methylureido)thiazole

HRID 1112054Notes

Reaction equation

HRID 1112054 reaction equation
[C:1]([C:5]1[S:9][C:8]([NH:10][C:11]([CH2:13][C:14]2[N:15]=[C:16]([NH2:19])[S:17][CH:18]=2)=[O:12])=[N:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:20][N:21]=[C:22]=[O:23]>N1C=CC=CC=1>[C:1]([C:5]1[S:9][C:8]([NH:10][C:11]([CH2:13][C:14]2[N:15]=[C:16]([NH:19][C:22]([NH:21][CH3:20])=[O:23])[S:17][CH:18]=2)=[O:12])=[N:7][N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 213211484-(5-Tert-butyl-1,3,4-thiadiazol-2-ylcarbamoylmethyl)-2-aminothiazole

Product 1

HCID 213211504-(5-Tert-butyl-1,3,4-thiadiazol-2-ylcarbamoylmethyl)-2-(3-methylureido)thiazoleYield 70.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A reaction mixture comprising 3.0 g (0.01 mole) of 4-(5-tert-butyl-1,3,4-thiadiazol-2-ylcarbamoylmethyl)-2-aminothiazole, 50 ml of pyridine and 0.8 g (0.014 mole) of methyl isocyanate was heated at 35°-37° for four hours. The reaction solution was allowed to stand over the weekend at ambient temperature. Most of the pyridine was removed by employing a rotary evaporator. The residue was mixed with hexane and the crude solid was collected. The filter cake was well washed with ethyl acetate. There was obtained 2.5 g of product, m.p. 190° (dec.). N.M.R. (dimethyl-d6 sulfoxide) ∂ 1.4 [C(CH3)3 ], 2.6 (CH3 doublet), 3.7 (CH2), 6.7 (hetero-aromatic).

Workup

  1. customto stand over the weekend at ambient temperature
  2. customMost of the pyridine was removed
  3. customa rotary evaporator
  4. additionThe residue was mixed with hexane
  5. customthe crude solid was collected
  6. washThe filter cake was well washed with ethyl acetate

Sources & evidence

ORD record
ord-8e8b27b68ec14743bb440fe65a8dd70c
Source dataset
uspto-grants-1978_10
Patent number
US04120690

Reaction notes

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