Potassium bis(trimethylsilyl)amide → HCID 474627, compound

HRID 580828Notes

Reaction equation

HRID 580828 reaction equation
Cl[C:2]1[C:7]([C:8]2[N:9]=[N:10][S:11][C:12]=2[C:13]2[C:14]([NH:19][CH2:20][CH3:21])=[N:15][CH:16]=[CH:17][CH:18]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+]>O1CCCC1.C(OCC)(=O)C>[CH3:21][CH2:20][N:19]1[C:14]2[N:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C:12]2[S:11][N:10]=[N:9][C:8]=2[C:7]2[CH:6]=[CH:5][CH:4]=[N:3][C:2]1=2

Participants

5

Reactant 2

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 57099143HCID 57099143, compound

Product 1

HCID 474627HCID 474627, compoundYield 73.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(2-chloropyridin-3-yl)-5-(2-ethylaminopyridin-3-yl)-1, 2, 3-thiadiazole (0.700 g) in tetrahydrofuran (5 mL) was added potassium bistrimethylsilylamide (0.5M in toluene, 3.5 mL). After 10 minutes the mixture was diluted with ethyl acetate, washed with water, dried, filtered and evaporated. Chromatography of the residue over silica gel gave 8-ethyl-(1, 2, 3)thiadiazolo[4',5':6,5]dipyrido[2,3-b:3',2'-f]azepine (0.453 g). mp 194-196° C.

Workup

  1. washwashed with water
  2. customdried
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-a046ebc701a043e59042a455a08363c5
Source dataset
uspto-grants-1999_07
Patent number
US05919779

Reaction notes

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