Methanimidamide, hydrochloride (1:1) → HCID 67397995, compound

HRID 1990708Notes

Reaction equation

HRID 1990708 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[C:9]#[C:10][CH2:11][CH2:12][CH2:13][O:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)=[CH:4][CH:3]=1.Cl.[CH:23]([NH2:25])=[NH:24]>C(#N)C.O.C(=O)([O-])[O-].[Na+].[Na+]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([CH2:11][CH2:12][CH2:13][O:14][CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][O:16]3)[N:25]=[CH:23][N:24]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 10313058Methanimidamide, hydrochloride (1:1)HCID 67398277HCID 67398277, compound

Product 1

HCID 67397995HCID 67397995, compoundYield 82.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolventHCID 10340Sodium CarbonateSolvent2×

Procedure

A mixture of 3.60 g (11.73 mmol) of 1-(4-chlorophenyl)-6-(tetrahydro-2H-pyran-2-yloxy)hex-2-yn-1-one, prepared in stage 5.2., of 9.45 g (117 mmol) of formamidine hydrochloride and of 25 g (234 mmol) of sodium carbonate in suspension in 108 ml of acetonitrile and 0.1 ml of water is stirred at 40° C. for 5 hours. The mixture is subsequently taken up in 600 ml of water and 400 ml of a saturated aqueous sodium carbonate solution. The organic phase is separated by settling, washed with 200 ml of water and 200 ml of a saturated aqueous sodium chloride solution, dried over sodium sulphate and evaporated. The residue is purified by chromatography on silica gel, elution being carried out with a 70/30 mixture of n-hexane and of ethyl acetate, to produce 3.22 g (9.67 mmol) of product in the form of a yellowish oil.

Workup

  1. customprepared in stage 5.2
  2. customThe organic phase is separated
  3. washwashed with 200 ml of water and 200 ml of a saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customThe residue is purified by chromatography on silica gel, elution
  7. additionbeing carried out with a 70/30 mixture of n-hexane and of ethyl acetate

Sources & evidence

ORD record
ord-4797da0c03d146029c313baaa1c13a03
Source dataset
uspto-grants-2010_01
Patent number
US07645757B2

Reaction notes

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