Water → HCID 22675413, compound

HRID 1005959Notes

Reaction equation

HRID 1005959 reaction equation
S(O[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18]1[N:22]([C:23]([CH3:25])=[CH2:24])[C:21]2[CH:26]=[CH:27][CH:28]=[CH:29][C:20]=2[N:19]=1)(C1C=CC(C)=CC=1)(=O)=O.[SH:30][C:31]1[NH:32][C:33]2[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=2[N:35]=1.C(N(CC)CC)C.O>C(#N)C>[N:32]1[C:33]2[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=2[NH:35][C:31]=1[S:30][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18]1[N:22]([C:23]([CH3:25])=[CH2:24])[C:21]2[CH:26]=[CH:27][CH:28]=[CH:29][C:20]=2[N:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 22675419HCID 22675419, compoundHCID 178527775HCID 178527775, compound

Product 1

HCID 22675413HCID 22675413, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.415 g of the compound obtained in Example 14b and 0.15 g of 2-mercaptobenzimidazole were refluxed for 5 hours in 10 ml of acetonitrile solvent containing 0.15 g of triethylamine. After cooling to room temperature, the reaction mixture was added with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane) to obtain 0.28 g of the title compound (yield: 71%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane)

Sources & evidence

ORD record
ord-a8a50ec3c7c843e986936c467ca92756
Source dataset
uspto-grants-2004_09
Patent number
US06787561B1

Reaction notes

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