Diglyme → HCID 178433507, compound

HRID 1728331Notes

Reaction equation

HRID 1728331 reaction equation
[CH2:1]([O:8][CH2:9][N:10]1[C:14]([S:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:13]([CH3:22])[N:12]=[C:11]1Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O:25]CCOCCOC.C[O-].[Na+]>CO>[CH2:1]([O:8][CH2:9][N:10]1[C:14]([S:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:13]([CH3:22])[N:12]=[C:11]1[OH:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8150DiglymeHCID 10942334Sodium MethoxideHCID 19002942HCID 19002942, compound

Product 1

HCID 178433507HCID 178433507, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 15 mg of 1-benzyloxymethyl-2-bromo-4-methyl-5-phenylthioimidazole (I-20) (0.04 mmol), obtained in Example 20, and 3 ml of 2-methoxyethyl ether is added 1 ml of 1M sodium methoxide solution in methanol, and the resultant mixture is heated at 130° C. for 5 hours. After evaporating the 2-methoxyethyl ether, the residue is chromatographed on a column of silica gel, eluting with 3% methanol/methylene chloride. The crude product is recrystallized from ethyl acetate/isopropyl ether to give 9 mg of the product (I-28). Yield, 71%; mp. 147°-148° C.

Workup

  1. customAfter evaporating the 2-methoxyethyl ether
  2. customthe residue is chromatographed on a column of silica gel
  3. washeluting with 3% methanol/methylene chloride
  4. customThe crude product is recrystallized from ethyl acetate/isopropyl ether

Sources & evidence

ORD record
ord-951a8d48da6241f5a42cdfc3e6382375
Source dataset
uspto-grants-1994_07
Patent number
US05326780

Reaction notes

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