Dimethyl 5-aminoisophthalate → HCID 67174306, compound

HRID 2176729Notes

Reaction equation

HRID 2176729 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[CH2:16]([N:34]=[C:35]=[O:36])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]>CN(C)C=O>[CH2:16]([NH:34][C:35](=[O:36])[NH:1][C:2]1[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=[C:4]([CH:3]=1)[C:12]([O:14][CH3:15])=[O:13])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

4

Reactant 2

HCID 66831Dimethyl 5-aminoisophthalateHCID 66988Octadecyl isocyanate2×

Product 1

HCID 67174306HCID 67174306, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

Dimethyl 5-aminoisophthalate (obtained from Aldrich Chemical Co., Milwaukee, Wis., 0.441 g, 2.12 mmol) was dissolved in dry N,N-dimethylformamide (8 mL) in a 50 mL round-bottom flask under inert atmosphere. A 2.12 Molar solution of octadecylisocyanate (2.12 mmol) in dry N,N-dimethylformamide (1 mL) was then added dropwise. The residual octadecylisocyanate solution was quantitatively transferred with 2 portions of N,N-dimethylformamide (1 mL each) and the reaction was stirred overnight at room temperature. The reaction was then heated to 100° C. for 22 h, and thereafter cooled to room temperature to give a white slurry. The solid was then vacuum filtered, washed with fresh N,N-dimethylformamide, and then washed with deionized water. The filtrate was concentrated by rotary evaporation to give a white solid.

Workup

  1. temperatureThe reaction was then heated to 100° C. for 22 h
  2. temperaturecooled to room temperature
  3. customto give a white slurry
  4. filtrationvacuum filtered
  5. washwashed with fresh N,N-dimethylformamide
  6. washwashed with deionized water
  7. concentrationThe filtrate was concentrated by rotary evaporation
  8. customto give a white solid

Sources & evidence

ORD record
ord-7207cd5d2c0e4e33933dd6b34e5dfbd2
Source dataset
uspto-grants-2015_06
Patent number
US09067878B2

Reaction notes

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