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

HRID 261762Notes

Reaction equation

HRID 261762 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-1b501202e94f466191bd3b8199fa3d73
Source dataset
uspto-grants-1979_05
Patent number
US04152329

Reaction notes

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