Ethanol → 4-(5-Tert-butyl-1,3,4-thiadiazol-2-ylcarbamoylmethyl)-2-aminothiazole

HRID 261760Notes

Reaction equation

HRID 261760 reaction equation
[C:1]([C:5]1[S:9][C:8]([NH:10][C:11](=[O:17])[CH2:12][C:13]([CH2:15]Br)=O)=[N:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].C(O)C.[NH2:21][C:22]([NH2:24])=[S:23].C(=O)(O)[O-].[Na+]>O>[C:1]([C:5]1[S:9][C:8]([NH:10][C:11]([CH2:12][C:13]2[N:21]=[C:22]([NH2:24])[S:23][CH:15]=2)=[O:17])=[N:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 2723790ThioureaHCID 21321151N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-4-bromoacetoacetamide

Product 1

HCID 213211484-(5-Tert-butyl-1,3,4-thiadiazol-2-ylcarbamoylmethyl)-2-aminothiazoleYield 96.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A reaction mixture comprising 11.2 g (0.035 mole) of N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-4-bromoacetoacetamide, 200 ml of ethanol and 2.8 g (0.037 mole) of thiourea was refluxed for three hours. The reaction solution was cooled and added to 300 ml of water. With stirring, there was slowly added an excess of saturated aqueous sodium bicarbonate. The product was collected and dried. There was obtained 10 g (96.2%) of white solid, m.p. 226° (dec.). N.M.R. (dimethyl-d6 sulfoxide) ∂ 1.4 [C(CH3)3 ], 3.6 (CH2), 6.3 (hetero-aromatic), 6.9 (NH).

Workup

  1. temperatureThe reaction solution was cooled
  2. customThe product was collected
  3. customdried

Sources & evidence

ORD record
ord-7c946d3f454f483489af2b83430ccd06
Source dataset
uspto-grants-1979_05
Patent number
US04152329

Reaction notes

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