Triethylamine → HCID 72382356, compound

HRID 1829040Notes

Reaction equation

HRID 1829040 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C:10](=[C:14]1[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][C:15]1=[O:23])[O:9][CH2:8]2.C(N(CC)CC)C.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>C1COCC1>[O:23]=[C:15]1[C:14](=[C:10]2[C:11]3[C:7](=[CH:6][C:5]([CH2:4][CH2:3][CH2:2][O:1][S:32]([CH3:31])(=[O:34])=[O:33])=[CH:13][CH:12]=3)[CH2:8][O:9]2)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 69659336HCID 69659336, compound

Product 1

HCID 72382356HCID 72382356, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 3-[5-(3-hydroxy-propyl)-3H-isobenzofuran-1-ylidene]-1,3-dihydro-indol-2-one (440 mg, 1.43 mmol) and triethylamine (289 mg, 2.86 mmol) in THF (7 ml), was added methanesulfonyl chloride (327 mg, 2.86 mmol). The mixture was stirred for 20 minutes and poured into an ice water (150 ml, containing 0.5 ml of AcOH). The solid was filtered, washed with water and dried under vacuum to afford a crude product. The crude product was purified by silica gel column chromatography, eluted with 5% MeOH in CHCl3, to give methanesulfonic acid 3-[1-(2-oxo-1,2-dihydro-indol-3-ylidene)-1,3-dihydro-isobenzofuran-5-yl]-propyl ester as a yellow solid (437 mg, 79%).

Workup

  1. filtrationThe solid was filtered
  2. washwashed with water
  3. customdried under vacuum
  4. customto afford a crude product
  5. customThe crude product was purified by silica gel column chromatography
  6. washeluted with 5% MeOH in CHCl3

Sources & evidence

ORD record
ord-c69a7ccfdad648b98141134adf325251
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

Loading…