Triethylamine → HCID 135407197, compound

HRID 466057Notes

Reaction equation

HRID 466057 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([C:16]([NH:18][NH2:19])=[S:17])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])[CH3:3].C(N(CC)CC)C.[C:27](C1NC=CN=1)(C1NC=CN=1)=[O:28]>O1CCCC1.CCOCC>[CH3:14][C:12]([C:9]1[CH:8]=[C:7]([C:16]2[S:17][C:27](=[O:28])[NH:19][N:18]=2)[CH:6]=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[C:10]=1[OH:11])([CH3:13])[CH3:15]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 136403396HCID 136403396, compound

Product 1

HCID 135407197HCID 135407197, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 3,5-bis(1,1-dimethylethyl)-4-hydroxy-benzene carbothioic acid, hydrazide (2.0 g, 0.0072 mole) in tetrahydrofuran (10 ml) is added triethylamine (0.39 g, 0.0039 mole) followed by carbonyl diimidazole (0.8 g, 0.0048 mole). The resulting mixture is stirred at 0° C. for one hour. Dilute with ether and extract product with 1M NaOH (2×). The combined aqueous layers are combined and made acidic with aqueous 6M HCl. The product is extracted with 1:1 ether/ethyl acetate. The combined organic extracts are washed with saturated aqueous NaCl and concentration in vacuo provides 1.4 g (2.2 g theor., 64%) of 5-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-1,3,4-thiadiazol-2(3H)-one after recrystallization from ethyl acetate/hexane: mp 229° C.

Workup

  1. extractionextract product with 1M NaOH (2×)
  2. extractionThe product is extracted with 1:1 ether/ethyl acetate
  3. washThe combined organic extracts are washed with saturated aqueous NaCl and concentration in vacuo

Sources & evidence

ORD record
ord-f98257c638fd4df5b948c44538ce8faf
Source dataset
uspto-grants-1992_10
Patent number
US05155122

Reaction notes

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