Dicyclohexylcarbodiimide → HCID 19742818, compound

HRID 2254617Notes

Reaction equation

HRID 2254617 reaction equation
[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([I:20])[CH:15]=2)[CH:3]=1.O.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.[NH2:47][CH:48]1[CH:53]2[CH2:54][CH2:55][N:50]([CH2:51][CH2:52]2)[CH2:49]1>CN(C)C=O>[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([NH:47][CH:48]2[CH:53]3[CH2:54][CH2:55][N:50]([CH2:51][CH2:52]3)[CH2:49]2)=[O:8])=[C:4]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([I:20])[CH:15]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 1232383-AminoquinuclidineHCID 27960291-Hydroxybenzotriazole hydrateHCID 19742819HCID 19742819, compound

Product 1

HCID 19742818HCID 19742818, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A mixture of 4-amino-5-chloro-2-[(3-iodophenyl)methoxy]benzoic acid (3.23 g, 8 mmol) and 1-hydroxybenzotriazole hydrate (1.23 g, 8 mmol) in anhydrous N, N-dimethylformamide (6 mL) under nitrogen was stirred for 30 minutes, treated with 1,3-dicyclohexylcarbodiimide (1.71 g, 8.3 mmol) in anhydrous N,N-dimethylformamide (2 mL), and stirred for 2 hours. A solution of 3-aminoquinuclidine (1.52 g, 12 mmol) in anhydrous N,N-dimethylformamide (4 mL) was added, and the mixture was stirred for 18 hours, filtered, and the filtrate concentrated in vacuo. The residue was dissolved in 20% methanol/tetrahydrofuran and filtered through a short column of alumina (eluted with 20% methanol/tetrahydrofuran). The filtrate was concentrated in vacuo and the residue was triturated from acetonitrile and recrystallized (2 crops) from 95% ethanol to afford 1.25 g (31%) of colorless solid; mp 196°-197° C.

Workup

  1. stirringstirred for 2 hours
  2. stirringthe mixture was stirred for 18 hours
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated in vacuo
  5. dissolutionThe residue was dissolved in 20% methanol/tetrahydrofuran
  6. filtrationfiltered through a short column of alumina (eluted with 20% methanol/tetrahydrofuran)
  7. concentrationThe filtrate was concentrated in vacuo
  8. customthe residue was triturated from acetonitrile
  9. customrecrystallized (2 crops) from 95% ethanol

Sources & evidence

ORD record
ord-a5ac6030ea9a4b64b26b9f05adec53b0
Source dataset
uspto-grants-1993_08
Patent number
US05236931

Reaction notes

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