Ethanol → HCID 21321159, compound

HRID 261761Notes

Reaction equation

HRID 261761 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 21321159HCID 21321159, compoundYield 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 four 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 four hours
  2. customThe product was isolated
  3. customdried

Sources & evidence

ORD record
ord-d582eac5f7a14c52b888cef17df73c51
Source dataset
uspto-grants-1979_05
Patent number
US04152329

Reaction notes

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