Methylamine → HCID 135786554, compound

HRID 1493014Notes

Reaction equation

HRID 1493014 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].CN.[CH2:27]([N:29](CC)CC)C>C(O)C>[CH3:21][C:20]([C:7]1[CH:8]=[C:9]([C:11]2[S:12][C:13]([NH:29][CH3:27])=[N:14][N:15]=2)[CH:10]=[C:5]([C:2]([CH3:4])([CH3:3])[CH3:1])[C:6]=1[OH:24])([CH3:22])[CH3:23]

Participants

5

Reactant 3

HCID 6329Methylamine2×HCID 8471TriethylamineHCID 135786529HCID 135786529, compound

Product 1

HCID 135786554HCID 135786554, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2,6-bis(1,1-dimethylethyl)-4-[5-(methylsulfonyl)-1,3,4-thiadiazole-2-yl]phenol (2.0 g, 0.0054 mole) in ethanol (10 ml) is added 25% ethanolic methylamine solution (15 ml), followed by triethylamine (0.6 g, 0.006 mole). The resulting mixture is heated to reflux for three hours. An additional amount of 25% ethanolic methylamine (15 ml) solution is added and the mixture is stirred overnight at reflux. The solution is cooled and the volatiles removed under reduced pressure. The residue is purified by flash chromatography (SiO2) using 30% ethyl acetate/hexane eluent. Recrystallize from ethyl acetate/hexane to obtain 0.8 g (1.7 g theor., 48%) of 2,6-bis(1,1-dimethylethyl)-4-[5-(methylamino)-1,3,4-thiadiazol-2-yl]phenol, mp 207.5°-208° C.

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureto reflux for three hours
  3. temperatureat reflux
  4. temperatureThe solution is cooled
  5. customthe volatiles removed under reduced pressure
  6. customThe residue is purified by flash chromatography (SiO2)
  7. customRecrystallize from ethyl acetate/hexane

Sources & evidence

ORD record
ord-cbcc6073f7e445ec9f5f35331ffb9a3d
Source dataset
uspto-grants-1994_12
Patent number
US05376670

Reaction notes

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