Triethylamine → HCID 135786534, compound

HRID 1493015Notes

Reaction equation

HRID 1493015 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].[N:25]#[C:26][NH2:27].C(N(CC)CC)C>CN(C=O)C.O>[CH3:22][C:20]([C:7]1[CH:8]=[C:9]([C:11]2[S:12][C:13]([NH:27][C:26]#[N:25])=[N:14][N:15]=2)[CH:10]=[C:5]([C:2]([CH3:3])([CH3:1])[CH3:4])[C:6]=1[OH:24])([CH3:23])[CH3:21]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 9864Cyanamide2×HCID 135786529HCID 135786529, compound

Product 1

HCID 135786534HCID 135786534, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2,6-bis(1,1-dimethylethyl)-4-[5-(methylsulfonyl)-1,3,4-thiadiazol-2-yl]phenol (5.0 g, 0.0136 mole) in a mixture of DMF (20 ml) and water (5 ml) is added cyanamide (5.0 g, 0.119 mole) and triethylamine (1.4 g, 0.0136 mole). The mixture is heated to 80° C. and stirred overnight. An additional portion of cyanamide (2.5 g, 0.059 mole) is added and the mixture is stirred six hours at 80° C. The reaction is cooled and partitioned between water and ether. The aqueous layer is acidified with 6M HCl (40 ml). The resulting precipitate is filtered and recrystallized from acetonitrile/water to provide 3.4 g of [5-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-1,3,4-thiadiazole-2-yl]cyanamide (4.5 g theor., 76%) after drying in vacuo at 70° C., mp >250° C.

Workup

  1. stirringthe mixture is stirred six hours at 80° C
  2. temperatureThe reaction is cooled
  3. custompartitioned between water and ether
  4. filtrationThe resulting precipitate is filtered
  5. customrecrystallized from acetonitrile/water

Sources & evidence

ORD record
ord-57d38eec981046ceadfd316957b6bacd
Source dataset
uspto-grants-1994_12
Patent number
US05376670

Reaction notes

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