2-Methylpropylenediamine → HCID 22147743, compound

HRID 2119824Notes

Reaction equation

HRID 2119824 reaction equation
[C:1]([C:3]1[CH:18]=[CH:17][C:6]([O:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)=[CH:5][CH:4]=1)#[N:2].[NH2:19][CH2:20][C:21]([NH2:24])([CH3:23])[CH3:22]>C1COCC1>[NH2:24][C:21]([CH3:23])([CH3:22])[CH2:20][NH:19][C:12](=[O:14])[C:11]1[CH:10]=[CH:9][C:8]([O:7][C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:18][CH:17]=2)=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 131282-MethylpropylenediamineHCID 21798064-(4-cyanophenoxy)benzoic acid

Product 1

HCID 22147743HCID 22147743, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(4′-Cyanophenoxy)benzoic acid (1.00 g, 4.2 mmol) was dissolved in THF (40 mL) followed by the addition of 1,1-carbonyldiimidazole (0.745 g, 4.6 mmol) in small portions. This mixture was stirred for 1 hour whereupon 1,2-diamino-2-methylpropane (0.48 mL, 4.6 mmol) was added and the resultant mixture stirred for 20 hours at RT. The mixture was then concentrated in vacuo and the residue chromatographed over silica (10% MeOH/CHCl3) to provide 0.50 g (38%) of the desired product. MS. (FD+) 310.2 m.p. 133-137° C.

Workup

  1. additionwas added
  2. concentrationThe mixture was then concentrated in vacuo
  3. customthe residue chromatographed over silica (10% MeOH/CHCl3)

Sources & evidence

ORD record
ord-d2765db21cb74d74a5434d2f24500ef3
Source dataset
uspto-grants-2004_02
Patent number
US06686372B2

Reaction notes

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