Diethyl Ether → HCID 10686834, compound

HRID 1872040Notes

Reaction equation

HRID 1872040 reaction equation
C(C1[CH:8]=[CH:7][C:6]([N:9]([CH2:18][CH3:19])[C:10]2[N:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH3:17])[N:11]=2)=[C:5]([S:20][CH3:21])[CH:4]=1)#N.[CH3:22][Mg]I.CC[O:27][CH2:28][CH3:29]>C1C=CC=CC=1>[C:28]([C:29]1[CH:8]=[CH:7][C:6]([N:9]([CH2:18][CH3:19])[C:10]2[N:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH3:17])[N:11]=2)=[C:5]([S:20][CH3:21])[CH:4]=1)(=[O:27])[CH3:22]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 18323838HCID 18323838, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 10686834HCID 10686834, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
25 °C

Procedure

To 0.5 g (1.68 mmoles) of the nitrile of Example 52 in 10 mL dry C6H6 was added 1.1 mL (3.3 mmoles) of a 3 M solution CH3MgI in ether and the mixture was stirred at 25° C. for 2 h and at reflux for 1 h. The reaction was quenched with water and 10% HCl and stirred for 20 min before 1 M NaOH was added until the solution was alkaline and the mixture was extracted with 100 mL EtOAc. The organic layer was washed with water, brine, dried and stripped in vacuo. The residue was chromatographed on silica gel using 20% EtOAc/hexanes to give 370 mg product (70% yield); mp 125-126° C. Elemental analysis for C17H21N3OS: Theory C: 64.73, H: 6.71 , N: 13.32, S: 10.16. Found C: 64.53, H: 6.73, N: 13.08. S: 10.19.

Workup

  1. temperatureat reflux for 1 h
  2. customThe reaction was quenched with water and 10% HCl
  3. stirringstirred for 20 min before 1 M NaOH
  4. additionwas added until the solution
  5. extractionthe mixture was extracted with 100 mL EtOAc
  6. washThe organic layer was washed with water, brine
  7. customdried
  8. customThe residue was chromatographed on silica gel using 20% EtOAc/hexanes

Sources & evidence

ORD record
ord-d6d401c1d4614c4fa2ce739b4524b33c
Source dataset
uspto-grants-2000_08
Patent number
US06107301

Reaction notes

Loading…