1,1-Dichloroethane → HCID 86686826, compound

HRID 2276782Notes

Reaction equation

HRID 2276782 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[S:14][C:13]([C:15]2[N:20]=[N:19][C:18](N)=[N:17][CH:16]=2)=[N:12][CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Cl:22]C(Cl)C.N(OC(C)(C)C)=O>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC>[Si:1]([O:8][CH2:9][C:10]1[S:14][C:13]([C:15]2[N:20]=[N:19][C:18]([Cl:22])=[N:17][CH:16]=2)=[N:12][CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 63651,1-DichloroethaneHCID 10906Tert-Butyl nitriteHCID 67454331HCID 67454331, compound

Product 1

HCID 86686826HCID 86686826, compound

Reagents, catalysts & solvents 1

HCID 70681Tetrabutylammonium ChlorideCatalyst

Conditions

Temperature
75 °C

Procedure

To a vial was added 6-(5-((tert-butyldimethylsilyloxy)methyl)thiazol-2-yl)-1,2,4-triazin-3-amine (2.5 g, 10.7 mmol), tetrabutylammonium chloride (6.3 g, 27.7 mmol) and dichloroethane (25 mL). The mixture was heated to 75° C., followed by the addition of t-butyl nitrite (3.3 mL, 27.7 mmol). The reaction was stirred at 75° C. for 3 h, followed by cooling to rt, quenching with brine (200 mL). The reaction was extracted four times with CH2Cl2. The combined organic layers were dried over Na2SO4, concentrated, and purified using silica gel chromatography to afford the 1.1 g of the title compound as an off-white solid.

Workup

  1. temperatureby cooling to rt
  2. customquenching with brine (200 mL)
  3. extractionThe reaction was extracted four times with CH2Cl2
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated
  6. custompurified

Sources & evidence

ORD record
ord-d7f8ae5a1a6649d0931872a949891995
Source dataset
uspto-grants-2015_09
Patent number
US09133123B2

Reaction notes

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