2-Amino-2-methyl-1-propanol → HCID 71283508, compound

HRID 529434Notes

Reaction equation

HRID 529434 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([C:11]([OH:13])=O)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.O=S(Cl)Cl.[NH2:18][C:19]([CH3:23])([CH3:22])[CH2:20][OH:21].CC[N:26](C(C)C)[CH:27]([CH3:29])[CH3:28].[C:33]([O-:36])(O)=O.[Na+]>CN(C=O)C.C(Cl)Cl>[Br:1][C:2]1[CH:10]=[C:9]([C:11]([NH:26][C:27]([CH3:29])([CH3:28])[CH2:33][OH:36])=[O:13])[CH:8]=[CH:7][C:3]=1[C:4]([NH:18][C:19]([CH3:23])([CH3:22])[CH2:20][OH:21])=[O:6]

Participants

8

Reactant 5

HCID 118072-Amino-2-methyl-1-propanolHCID 24386Thionyl ChlorideHCID 68513Bromoterephthalic acidHCID 81531DiisopropylethylamineHCID 516892Sodium Bicarbonate

Product 1

HCID 71283508HCID 71283508, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

2-Bromoterephthalic acid (750 mg, 3.06 mmol, 1 eq.) was suspended into SOCl2 (5 ml) in the presence of DMF (1 drop), and the solution was refluxed for 3 hr. After cooling to room temperature, evaporating and dried in vacuo, the resulting compound was dissolved in CH2Cl2 (10 ml), and was dropped into a solution of 2-amino-2-methylpropan-1-ol (750 mg, 8.41 mmol, 2.7 eq.) and DIEA (1.5 ml) in CH2Cl2 (10 ml), and the solution was stirred at room temperature overnight. Saturated NaHCO3 aqueous solution was added to the reaction mixture and extracted with EtOAc (×3), and combined organic phase was washed with water and brine, dried over Na2SO4, filtered and evaporated to obtain 2-bromo-N1,N4-bis(1-hydroxy-2-methylpropan-2-yl)terephthalamide 4b as a white solid. (922 mg, 78%)

Workup

  1. temperaturethe solution was refluxed for 3 hr
  2. customevaporating
  3. customdried in vacuo
  4. dissolutionthe resulting compound was dissolved in CH2Cl2 (10 ml)
  5. extractionextracted with EtOAc (×3), and combined organic phase
  6. washwas washed with water and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-233dda166ab44b1491aea887112cf636
Source dataset
uspto-grants-2016_05
Patent number
US09346957B2

Reaction notes

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