Water → 4-(5-Tert-butyl-1,3,4-thiadiazol-2-ylcarbamoylmethyl)-2-(1,3-dimethylureido)thiazole

HRID 1112056Notes

Reaction equation

HRID 1112056 reaction equation
[C:1]([C:5]1[S:9][C:8]([NH:10][C:11]([CH2:13][C:14]2[N:15]=[C:16]([NH:19][CH3:20])[S:17][CH:18]=2)=O)=[N:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:21][N:22]=[C:23]=[O:24].[OH2:25]>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]([N:19]([CH3:20])[C:23]([NH:22][CH3:21])=[O:24])[S:17][CH:18]=2)=[O:25])=[N:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 12228Methyl IsocyanateHCID 213211594-(5-Tert-butyl-1,3,4-thiadiazol-2-ylcarbamoylmethyl)-2-methylaminothiazole

Product 1

HCID 213211624-(5-Tert-butyl-1,3,4-thiadiazol-2-ylcarbamoylmethyl)-2-(1,3-dimethylureido)thiazole

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A 4.0 g sample (0.013 mole) of 4-(5-tert-butyl-1,3,4-thiadiazol-2-ylcarbamoylmethyl)-2-methylaminothiazole was dissolved in 30 ml of pyridine and 1.1 g (0.02 mole) of methyl isocyanate was added. The solution was stirred and heated at 50° for 12 hours. Water was added and the mixture was stirred for 2 hours at ice-bath temperatures. After most of the oil-like material had crystallized, the product was collected and washed with water. There was obtained 3.2 g of white solid, m.p. 175°-77°. N.M.R. (CDCl3) ∂ 1.5 [C(CH3)3 ], 2.7-2.9 (CH3, doublet), 3.4 (CH3, singlet), 4.1 (CH2), 6.9 (hetero-aromatic).

Workup

  1. temperatureheated at 50° for 12 hours
  2. stirringthe mixture was stirred for 2 hours at ice-bath temperatures
  3. customAfter most of the oil-like material had crystallized
  4. customthe product was collected
  5. washwashed with water

Sources & evidence

ORD record
ord-3377fed9983e43df9e6dab92868740f9
Source dataset
uspto-grants-1978_10
Patent number
US04120690

Reaction notes

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