Sodium Chloride → HCID 54401809, compound

HRID 842605Notes

Reaction equation

HRID 842605 reaction equation
S(Cl)(Cl)=O.[C:5]([NH:8][C:9]1[C:16]([OH:17])=[C:15]([O:18][CH3:19])[CH:14]=[CH:13][C:10]=1[CH2:11]O)(=O)[CH3:6].[C-:20]#[N:21].[K+].C1OCCOCCOCCOCCOCCOC1.[Na+].[Cl-]>C1(C)C=CC=CC=1.CN(C=O)C.C(Cl)Cl>[CH3:6][C:5]1[O:17][C:16]2[C:15]([O:18][CH3:19])=[CH:14][CH:13]=[C:10]([CH2:11][C:20]#[N:21])[C:9]=2[N:8]=1

Participants

9

Reactant 5

HCID 5234Sodium ChlorideHCID 9032Potassium CyanideHCID 24386Thionyl ChlorideHCID 2855718-Crown-6HCID 53682417HCID 53682417, compound

Product 1

HCID 54401809HCID 54401809, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (40 ml) is slowly added at 0° C. with stirring to a suspension of 2-acetamido-3-hydroxy-4-methoxybenzyl alcohol (2.5 g, 12.0 mmol) and anhydrous CH2Cl2 (30 ml). After the reaction mixture has warmed to RT, it is stirred for 1 h and then stirred at 50° C. for a further 1.5 h. The reaction solution is concentrated in vacuo and then coevaporated with toluene (3 times). The residue obtained is dissolved in a mixture of toluene and DMF (8:1, 45 ml) and added dropwise to a solution of KCN (1.0 g, 15.4 mmol) in 18-crown-6 (4.07 g, 15.4 mmol) and absolute DMF (55 ml). The reaction solution is stirred overnight at RT and then poured into a half-concentrated aqueous NaCl solution, extracted with ethyl acetate (5 times), dried over MgSO4, filtered off and concentrated in vacuo. For further purification, the crude product is filtered through a silica gel column [petroleum ether/ethyl acetate (6:4)]. The title compound is obtained as colorless crystals (1.28 g). TLC, silica gel (glass plates), petroleum ether/ethyl acetate (6:4), Rf=0.32.

Workup

  1. stirringstirred at 50° C. for a further 1.5 h
  2. concentrationThe reaction solution is concentrated in vacuo
  3. customThe residue obtained
  4. stirringThe reaction solution is stirred overnight at RT
  5. extractionextracted with ethyl acetate (5 times)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered off
  8. concentrationconcentrated in vacuo
  9. customFor further purification
  10. filtrationthe crude product is filtered through a silica gel column [petroleum ether/ethyl acetate (6:4)]

Sources & evidence

ORD record
ord-c2b81e6ee1b84b9a8a474b2bc38a01e9
Source dataset
uspto-grants-2002_04
Patent number
US06376485B1

Reaction notes

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