Hydrochloric Acid → HCID 178418923, compound

HRID 2416634Notes

Reaction equation

HRID 2416634 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:8]#[C:9][NH2:10].Cl.O1CCOCC1>O.C(OCC)C>[C:2]1([NH:1][C:9]([NH2:10])=[NH:8])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 9864CyanamideHCID 312751,4-Dioxane

Product 1

HCID 178418923HCID 178418923, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

Aniline (30 mmol, 1 equiv.), cyanamide (1.3 g, 31 mmol, 1.03 equiv.), and 4N hydrogen chloride in dioxane (8 mL, 32 mmol) was stirred for 10 minutes at room temperature and heated to 80° C. for 18 hours. The mixture was diluted with water (30 mL) and diethyl ether (50 mL). The aqueous layer was washed with ether (30 mL) and the organic layers were discarded. The aqueous layer was neutralized with 6N aqueous HCl (6 mL) and diluted with ethyl acetate (50 mL). The aqueous layer was extracted with ethyl acetate (50 mL) four times. The combined organic layers were concentrated under reduced pressure to afford a solid compound. The solid was washed with diethyl ether (30 mL) to provide pale yellow title compound. The compound was characterized by LC/MS and HPLC.

Workup

  1. washThe aqueous layer was washed with ether (30 mL)
  2. additiondiluted with ethyl acetate (50 mL)
  3. extractionThe aqueous layer was extracted with ethyl acetate (50 mL) four times
  4. concentrationThe combined organic layers were concentrated under reduced pressure
  5. customto afford a solid compound
  6. washThe solid was washed with diethyl ether (30 mL)

Sources & evidence

ORD record
ord-6a4b105bc44640c9b83fd98b4542916a
Source dataset
uspto-grants-2004_11
Patent number
US06825190B2

Reaction notes

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