Myristyl bromide → HCID 12051747, compound

HRID 2229353Notes

Reaction equation

HRID 2229353 reaction equation
[H-].[Na+].[C:3]1([NH:9][C:10]2[S:14][N:13]=[N:12][C:11]=2[C:15]([NH2:17])=[O:16])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].[K+].[Br-]>CN(C=O)C>[CH2:32]([N:9]([C:10]1[S:14][N:13]=[N:12][C:11]=1[C:15]([NH2:17])=[O:16])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH3:19]

Participants

6

Reactant 4

HCID 8208Myristyl bromideHCID 24758Sodium hydrideHCID 253877Potassium BromideHCID 5148325HCID 5148325, compound

Product 1

HCID 12051747HCID 12051747, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an ice-cooled suspension of NaH (19 mg, 60 wt % in oil, 0.46 mmole) in 3 mL of DMF was added 5-(N-phenylamino)-1,2,3-thiadiazole-4-carboxamide (100 mg, 0.46 mmole). The mixture was stirred at room temperature for 1 h. 1-Bromotetradecane (131 mg, 0.47 mmole) was then added to the reaction mixture which was cooled in ice bath. The reaction was carried out overnight with stirring and then quenched with a mixture of 5 mL of saturated aqueous NH4Cl 5 mL of saturated aqueous NaCl and 10 mL EtOAc. The aqueous layer was extracted with EtOAc (2×10 mL). The combined organic layers were dried with anhydrous Na2SO4, concentrated and then purified by preparative TLC with hexane-EtOAc (1:1) as the eluant. A white powder product was obtained (122 mg, 66%). m.p. 79-81° C. 1H NMR (ppm, CDCl3): 7.60-7.44 (m, 5H), 7.20 (s, br., 1H), 5.63 (s, br., 1H), 2.96 (t, 2H), 1.43-1.00 (m, 24H), 0.88 (t, 3H). FTIR (cm−1, KBr pellet): 3386, 3299, 2918, 2851, 1674, 1657, 1600, 1527, 1503, 1384, 1299, 999, 766, 743, 693.

Workup

  1. temperaturewas cooled in ice bath
  2. waitThe reaction was carried out overnight
  3. stirringwith stirring
  4. customquenched with a mixture of 5 mL of saturated aqueous NH4Cl 5 mL of saturated aqueous NaCl and 10 mL EtOAc
  5. extractionThe aqueous layer was extracted with EtOAc (2×10 mL)
  6. dry with materialThe combined organic layers were dried with anhydrous Na2SO4
  7. concentrationconcentrated
  8. custompurified by preparative TLC with hexane-EtOAc (1:1) as the eluant
  9. customA white powder product was obtained (122 mg, 66%)

Sources & evidence

ORD record
ord-5722f4889410452aa3e0feaee8f01041
Source dataset
uspto-grants-2002_07
Patent number
US06420400B1

Reaction notes

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