tert-Butanol → HCID 69359268, compound

HRID 852558Notes

Reaction equation

HRID 852558 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[CH:5]=1.[C:17](O)([CH3:20])([CH3:19])[CH3:18].CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[C:7]([O:9][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:8]

Participants

6

Reactant 3

HCID 6386tert-ButanolHCID 747761,3-Benzenedicarboxylic acid, 5-nitro-, 1-methyl esterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 69359268HCID 69359268, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 5-nitro-isophthalic acid monomethyl ester (D77) (5.0 g, 22.2 mmol, 1 equiv), tert-BuOH (8.2 g, 111 mmol, 5 equiv), EDAC.HCl (4.8 g, 25 mmol, 1.1 equiv) and DMAP (205 mg, 1.68 mmol, 0.07 equiv) dissolved in CH2Cl2 (50 ml) was stirred for 1 h at room temperature The mixture was then diluted with CH2Cl2 (50 ml), washed with 2N aqueous HCl solution (50 ml) and saturated aqueous NaHCO3 solution (50 ml), dried over MgSO4 and concentrated in vacuo to give of 5-nitro-isophthalic acid 1-tert-butyl ester 3-methyl ester (D78) (5.3 g, 85%) as a pale yellow oil.

Workup

  1. washwashed with 2N aqueous HCl solution (50 ml) and saturated aqueous NaHCO3 solution (50 ml)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dc2bd95a805e42e799e1bc6f5a23f911
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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