Ethanolamine → HCID 135786540, compound

HRID 1493016Notes

Reaction equation

HRID 1493016 reaction equation
[CH3:1][C:2]([C:5]1[CH:10]=[C:9]([C:11]2[S:12][C:13](S(C)(=O)=O)=[N:14][N:15]=2)[CH:8]=[C:7]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:6]=1[OH:24])([CH3:4])[CH3:3].[CH2:25]([CH2:27][NH2:28])[OH:26]>C(O)(C)C>[CH3:1][C:2]([C:5]1[CH:10]=[C:9]([C:11]2[S:12][C:13]([NH:28][CH2:27][CH2:25][OH:26])=[N:14][N:15]=2)[CH:8]=[C:7]([C:20]([CH3:22])([CH3:21])[CH3:23])[C:6]=1[OH:24])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 135786529HCID 135786529, compound

Product 1

HCID 135786540HCID 135786540, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 2,6-bis(1,1-dimethylethyl)-4-[5-(methylsulfonyl)-1,3,4-thiadiazole-2-yl]phenol (4.0 g, 0.0109 mole) in isopropyl alcohol (15 ml) is added ethanolamine (1.9 g, 0.0326 mole). The resulting mixture is heated to reflux for 18 hours. The reaction is cooled and concentrated in vacuo. The resulting solid is recrystallized from methanol/water to give 3.2 g (3.8 g theor., 83%) of 2,6-bis(1,1-dimethylethyl)-4-[5-[(2-hydroxyethyl)amino]-1,3,4-thiadiazol-2-yl]phenol after drying in vacuo at 65° C., mp 212°-213.5° C.

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureto reflux for 18 hours
  3. temperatureThe reaction is cooled
  4. concentrationconcentrated in vacuo
  5. customThe resulting solid is recrystallized from methanol/water

Sources & evidence

ORD record
ord-3a7e9461f8d24c02bdab3ac134d726a4
Source dataset
uspto-grants-1994_12
Patent number
US05376670

Reaction notes

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