Triethylamine → HCID 135786530, compound

HRID 1493035Notes

Reaction equation

HRID 1493035 reaction equation
[NH2:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:10]([OH:17])=[C:9]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:8]=2)=[N:4][N:3]=1.C(N(CC)CC)C.[CH3:29][S:30](Cl)(=[O:32])=[O:31].[OH-].[Na+]>C1(C)C=CC=CC=1>[CH3:16][C:13]([C:11]1[CH:12]=[C:7]([C:5]2[S:6][C:2]([NH:1][S:30]([CH3:29])(=[O:32])=[O:31])=[N:3][N:4]=2)[CH:8]=[C:9]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:10]=1[OH:17])([CH3:14])[CH3:15]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 135518175HCID 135518175, compound

Product 1

HCID 135786530HCID 135786530, compoundYield 29.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A slurry of 0.52 g (1.7 mmol) of 4-(5-amino-1,3,4-thiadiazol-2-yl]-2,6-bis(1,1-dimethylethyl)phenol and 0.26 g (2.58 mmol) of triethylamine in 6 ml of toluene is treated with 0.30 g (2.58 mmol) of methane sulfonylchloride and warmed at 95°-105° C. for 21 hours under Nitrogen atmosphere. The reaction is cooled to room temperature and poured onto cold aqueous 1N NaOH (100 ml) and extracted with t-butylmethyl ether (3×20 ml). The aqueous layer is acidified with aqueous 1N HCl and filtered to give a yellow solid. Recrystallization from absolute ethanol gives 0.19 g (0.65 g, theor., 29%) of N-[5-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-1,3,4-thiadiazol-2-yl]methanesulfonamide as a solid: mp 293°-294° C.

Workup

  1. temperaturewarmed at 95°-105° C. for 21 hours under Nitrogen atmosphere
  2. extractionextracted with t-butylmethyl ether (3×20 ml)
  3. filtrationfiltered
  4. customto give a yellow solid
  5. customRecrystallization from absolute ethanol

Sources & evidence

ORD record
ord-721b0455a995497785c94b1da4d6af99
Source dataset
uspto-grants-1994_12
Patent number
US05376670

Reaction notes

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