Hydrochloric Acid → HCID 69299496, compound

HRID 2196500Notes

Reaction equation

HRID 2196500 reaction equation
[C:1]([C:3]1[S:7][CH:6]=[C:5]([N:8](C(OC(C)(C)C)=O)[NH:9]C(OC(C)(C)C)=O)[CH:4]=1)#[N:2].[ClH:24].O1CCOCC1>CC(O)C>[ClH:24].[NH:8]([C:5]1[CH:4]=[C:3]([C:1]#[N:2])[S:7][CH:6]=1)[NH2:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 59843278Di-tert-butyl 1-(5-cyanothiophen-3-yl)hydrazine-1,2-dicarboxylate

Product 1

HCID 69299496HCID 69299496, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a stirring solution of compound 12 (1.38 g, 4.07 mmol) in 2-propanol (10 mL) was added 4M HCl in dioxane (10 mL, 40.0 mmol). The reaction heated to 80 degrees for 1 hour turning into a dark brown solution. The mixture was evaporated to dryness and the resulting the brown solid suspended and sonicated in diethyl ether. The suspension was filtered to afford compound 13 (0.701 g, 97%) as a brown solid. LRMS (ESI): calc. 139.0; found 140.1 (MH)+.

Workup

  1. temperatureThe reaction heated to 80 degrees for 1 hour
  2. customThe mixture was evaporated to dryness
  3. customsonicated in diethyl ether
  4. filtrationThe suspension was filtered

Sources & evidence

ORD record
ord-7e624a66ce7e4c598f259738cf1ddbb4
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

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