Guanidine Hydrochloride → HCID 57678441, compound

HRID 491496Notes

Reaction equation

HRID 491496 reaction equation
[I:1][C:2]1[CH:13]=[C:12]([O:14][CH3:15])[C:11]([I:16])=[CH:10][C:3]=1[O:4][C:5](=[CH:8]C)[C:6]#[N:7].Cl.NC1C=CC=CC=1.O(C)[Na].Cl.[NH2:29][C:30]([NH2:32])=[NH:31]>C(O)C.CO>[I:1][C:2]1[CH:13]=[C:12]([O:14][CH3:15])[C:11]([I:16])=[CH:10][C:3]=1[O:4][C:5]1[C:6]([NH2:7])=[N:29][C:30]([NH2:32])=[N:31][CH:8]=1

Participants

7

Reactant 4

HCID 5742Guanidine HydrochlorideHCID 8870Benzenamine hydrochloride (1:1)HCID 68839019HCID 68839019, compoundHCID 178418582HCID 178418582, compound

Product 1

HCID 57678441HCID 57678441, compoundYield 36.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 887MethanolSolvent

Conditions

Temperature
85 °C

Procedure

2-(2,5-Diiodo-4-methoxy-phenoxy)-but-2-enenitrile (3.47 g, 6.75 mmol) and aniline hydrochloride (3.5 g, 27 mmol) were dissolved in 27 mL ethanol. The reaction mixture was heated to 85° C. and stirred under nitrogen for 18 hours. The reaction mixture was cooled and 25% NaOCH3 in methanol (7.3 mL) was added, followed by guanidine hydrochloride (3.2 g), and ethanol (10 mL). The reaction mixture was heated to 100° C. for 21 hours, then cooled and concentrated under reduced pressure. The residue was poured into water and extracted with dichloromethane. The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to give 1.2 g of 5-(2,5-Diiodo-4-methoxy-phenoxy)-pyrimidine-2,4-diamine, MS (M+H)=485.

Workup

  1. temperatureThe reaction mixture was cooled
  2. temperatureThe reaction mixture was heated to 100° C. for 21 hours
  3. temperaturecooled
  4. concentrationconcentrated under reduced pressure
  5. additionThe residue was poured into water
  6. extractionextracted with dichloromethane
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c8a6a9147aa74e76860095c949d126ca
Source dataset
uspto-grants-2009_05
Patent number
US07531547B2

Reaction notes

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