Dicyclohexylcarbodiimide → HCID 54547844, compound

HRID 582286Notes

Reaction equation

HRID 582286 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:9][C:10]2[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=2C(O)=O)[CH:6]=[CH:7][CH:8]=1.[OH:19]N1C2C=CC=CC=2N=N1.N1CCCC1.C1(N=[C:41]=[N:42][CH:43]2CC[CH2:46][CH2:45][CH2:44]2)CCCCC1>C1COCC1.CC#N.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:9][C:10]2[CH:11]=[CH:15][C:16]([C:41]([N:42]3[CH2:43][CH2:44][CH2:45][CH2:46]3)=[O:19])=[CH:17][CH:18]=2)[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 31268PyrrolidineHCID 757711-HydroxybenzotriazoleHCID 119702Anthranilic acid, N-(3-methoxyphenyl)-

Product 1

HCID 54547844HCID 54547844, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 22177404Acetonitrile tetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2 g (8.2 mmol) of 4-[N-(3-methoxyphenyl)aminobenzoic acid, 2.2 g (16.4 mmol) of N-hydroxybenzotriazole and 1 ml (12.3 mmol) of pyrrolidine were dissolved in 40 ml of a 7:3 mixture of THF/CH3CN, under a nitrogen atmosphere. The solution was cooled to 0° C. and 3.4 g (16.4 mmol) of dicyclohexylcarbodiimide dissolved in 20 ml of CH2Cl2 were added. The reaction mixture was allowed to warm to room temperature during 1 h., stirred an additional hour, then the precipitate was filtered off and the solvent was removed in vacuo. The residue was taken up with water and extracted with AcOEt, the organic layer was dried over Na2SO4 and the solvent removed in vacuo. The resulting crude mixture was purified by flash chromatography (AcOEt), yielding 2.4 g of the title compound.

Workup

  1. additionwere added
  2. temperatureto warm to room temperature during 1 h.
  3. filtrationthe precipitate was filtered off
  4. customthe solvent was removed in vacuo
  5. extractionextracted with AcOEt
  6. dry with materialthe organic layer was dried over Na2SO4
  7. customthe solvent removed in vacuo
  8. customThe resulting crude mixture was purified by flash chromatography (AcOEt)

Sources & evidence

ORD record
ord-754f0d4c459c4e6083767e74408182d4
Source dataset
uspto-grants-1999_07
Patent number
US05922887

Reaction notes

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