Ethyl Acetate → HCID 86662545, compound

HRID 881787Notes

Reaction equation

HRID 881787 reaction equation
[CH3:1][C:2]1([CH3:24])[C:10]2[C:9]3[CH:11]=[C:12]([S:19]([O-:22])(=[O:21])=[O:20])[CH:13]=[C:14]([S:15]([O-:18])(=[O:17])=[O:16])[C:8]=3[CH:7]=[CH:6][C:5]=2[N:4]=[C:3]1[CH3:23].Br[CH:26]([CH2:30][CH2:31]CC)[C:27]([OH:29])=[O:28].[C:34](OCC)(=O)[CH3:35]>>[C:27]([CH:26]([CH2:30][CH3:31])[CH2:34][CH2:35][O:17][S:15]([C:14]1[C:8]2[CH:7]=[CH:6][C:5]3[NH+:4]=[C:3]([CH3:23])[C:2]([CH3:24])([CH3:1])[C:10]=3[C:9]=2[CH:11]=[C:12]([S:19]([O-:22])(=[O:21])=[O:20])[CH:13]=1)(=[O:18])=[O:16])([OH:29])=[O:28]

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 120132-Bromohexanoic acidHCID 86313550HCID 86313550, compound

Product 1

HCID 86662545HCID 86662545, compoundYield 70%

Conditions

Temperature
125 °C

Procedure

A suspension of 1,1,2-trimethylbenz[e]indol-6,8-disulfonate (4.82 g, 13.0 mmol), bromohexanoic acid (25 g, 130 mmol) in a 250 mL round bottom flask was heated in an oil bath at 125° C. for 40 h. After cooling to ambient temperature ethyl acetate (100 mL) was added the solid was triturated. Filtered to collect the solid, washed with ethyl acetate (3×50 mL), ether (2×20 mL) and dried. Further drying in an oven at 40° C. under high vacuum for 18 h gave 4.41 g (70.0%) of the product.

Workup

  1. additionwas added the solid
  2. customwas triturated
  3. filtrationFiltered
  4. customto collect the solid
  5. washwashed with ethyl acetate (3×50 mL), ether (2×20 mL)
  6. customdried
  7. customFurther drying in an oven at 40° C. under high vacuum for 18 h

Sources & evidence

ORD record
ord-fad047bb9d5740a88f2f0597b89f4fea
Source dataset
uspto-grants-2015_03
Patent number
US08993737B2

Reaction notes

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