Ammonia → HCID 136388363, compound

HRID 480715Notes

Reaction equation

HRID 480715 reaction equation
[C:1]([C:3]1[O:4][C:5]2[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:6]=2[CH:7]=1)#[N:2].Cl.CO.[NH3:16].[CH3:17][S:18]([OH:21])(=[O:20])=[O:19]>CO>[CH3:17][S:18]([OH:21])(=[O:20])=[O:19].[C:1]([C:3]1[O:4][C:5]2[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:6]=2[CH:7]=1)(=[NH:16])[NH2:2]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6395Methanesulfonic AcidHCID 18766634HCID 18766634, compoundHCID 21893726Hydrochloride methanol

Product 1

HCID 136388363HCID 136388363, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2Cyano-6-hydroxybenzofuran (Rene, L.; Buisson, J.-P.; Royer. R. Reaction induites par le chlorhydrate de pyridine. XVI. -Sur la desalcoylation des derives Bz-methoxyles de nitriles et amides coumariliques. Bull. Soc. Chim. 1974, 475-476; 1.45 g, 9.11 mmol) was added to a cooled, saturated methanol-HCl solution (10 mL) and the mixture was stirred for 20 h at ambient temperature. The reaction mixture was concentrated in vacuo to give a solid. The solid was suspended in anhydrous methanol (40 mL) and gaseous NH3 was introduced into the mixture at 50° C. for 3 h to give a homogenous solution. The solvent was evaporated in vacuo, and the resulting solid was suspended in methanol (10 mL) and then treated with a saturated solution of NaHCO3 (30 mL). The precipitate was collected by filtration, washed with water (15 mL) and then dried in vacuo over P2O5 for 3 h. The solid (1.48 g) was suspended in 5 mL of methanol and then treated with methanesulfonic acid (1.1 g, 11.5 mmol). The precipitated material was recrystallized from methanol to give 1.62 g (65%) of 2-amidino-6-hydroxybenzofuran methanesulfonate as a brown solid, mp 253-254° C.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto give a solid
  3. customto give a homogenous solution
  4. customThe solvent was evaporated in vacuo
  5. additiontreated with a saturated solution of NaHCO3 (30 mL)
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with water (15 mL)
  8. dry with materialdried in vacuo over P2O5 for 3 h
  9. customThe precipitated material was recrystallized from methanol

Sources & evidence

ORD record
ord-8c6cd96b036e4b55b83e2bfaa0affa1d
Source dataset
uspto-grants-2003_11
Patent number
US06653340B1

Reaction notes

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