Sulfuric Acid → HCID 19037364, compound

HRID 263503Notes

Reaction equation

HRID 263503 reaction equation
[C:1]1([CH2:7][O:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH2:18][CH2:19][C:20]2[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=2[C:22]([OH:24])=[O:23])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:29][C:30](=[CH2:32])[CH3:31].S(=O)(=O)(O)O>C(Cl)Cl>[C:1]1([CH2:7][O:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH2:18][CH2:19][C:20]2[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=2[C:22]([O:24][C:30]([CH3:32])([CH3:31])[CH3:29])=[O:23])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8255Isobutylene2×HCID 19037354HCID 19037354, compound

Product 1

HCID 19037364HCID 19037364, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-[2-(2-(phenylmethoxycarbonylamino)phenyl)ethyl]benzoic acid (5.2 g, 0.014 mol) in methylene chloride (100 mL) was treated with isobutylene (15 mL) and sulfuric acid (0.14 mL) and stirred at room temperature. Isobutylene was added over the period of several days until the reaction was complete. The reaction mixture was washed with 5% aqueous sodium carbonate and with water. The organic phase was dried with magnesium sulfate and concentrated in vacuo to give an oil which was purified by chromatography (silica gel, hexane:ethyl acetate 95:5) to give t-butyl 2-[2-(2-(phenylmethoxycarbonylamino)phenyl)-ethyl]-benzoate (1.8 g, 31%).

Workup

  1. washThe reaction mixture was washed with 5% aqueous sodium carbonate and with water
  2. dry with materialThe organic phase was dried with magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customto give an oil which
  5. customwas purified by chromatography (silica gel, hexane:ethyl acetate 95:5)

Sources & evidence

ORD record
ord-0ea26e969fcf40ffac0a7a8abf0e6ed6
Source dataset
uspto-grants-1997_07
Patent number
US05643872

Reaction notes

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