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

HRID 1112053Notes

Reaction equation

HRID 1112053 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.[CH3:21][NH:22][C:23]([NH2:25])=[S:24].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:25]=[C:23]([NH:22][CH3:21])[S:24][CH:15]=2)=[O:17])=[N:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 2723704MethylthioureaHCID 21321151N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-4-bromoacetoacetamide

Product 1

HCID 213211594-(5-Tert-butyl-1,3,4-thiadiazol-2-ylcarbamoylmethyl)-2-methylaminothiazoleYield 87.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A reaction mixture containing 11.4 g (0.035 mole) of N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-4-bromoacetoacetamide, 150 ml of ethanol and 3.3 g (0.036 mole) of N-methylthiourea was refluxed for 4 hours. The reaction solution was poured into 300 ml of water and treated with excess aqueous sodium bicarbonate. The product was isolated and dried. There was obtained 9.5 g (87.2%) of white solid, m.p. 198°-200° (dec.). N.M.R. (CDCl3) ∂ 1.4 [C(CH3)3 ], 3.0 (CH3), 3.8 (CH2), 6.4 (hetero-aromatic).

Workup

  1. temperaturewas refluxed for 4 hours
  2. customThe product was isolated
  3. customdried

Sources & evidence

ORD record
ord-a8c2fdfd9bff400d80dd3b5c329635a4
Source dataset
uspto-grants-1978_10
Patent number
US04120690

Reaction notes

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