Triethylamine → HCID 12805216, compound

HRID 1906223Notes

Reaction equation

HRID 1906223 reaction equation
[Cl-].[C:2]1([N:8](C2C=CC=CC=2)C([N+]2C=CC=CC=2)=O)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:23]=[C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26](=[O:33])[N:25]1[CH2:34][CH2:35][C:36]1[C:44]2[C:39](=[CH:40][CH:41]=[C:42]([CH2:45][C:46](O)=[O:47])[CH:43]=2)[NH:38][CH:37]=1.C(N(CC)CC)C>O>[O:23]=[C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26](=[O:33])[N:25]1[CH2:34][CH2:35][C:36]1[C:44]2[C:39](=[CH:40][CH:41]=[C:42]([CH2:45][C:46]([NH:8][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:47])[CH:43]=2)[NH:38][CH:37]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12486269HCID 12486269, compoundHCID 12805187HCID 12805187, compound

Product 1

HCID 12805216HCID 12805216, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An ice-cold solution of diphenylamino carbonyl pyridinium chloride (3.5 g) in water (35 ml) was added dropwise to a mixture of 3-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-1H-indole-5-acetic acid (3.5 g), triethylamine (2.8 ml) and ice-water (70 ml) with rapid stirring over 15 min. After stirring the mixture for a further 10 min. it was extracted with ethyl acetate (3×30 ml). The combined organic extracts were washed with water (1×50 ml), dried (Na2SO4), and evaporated in vacuo to give an orange solid (3.6 g).

Workup

  1. stirringAfter stirring the mixture for a further 10 min. it
  2. extractionwas extracted with ethyl acetate (3×30 ml)
  3. washThe combined organic extracts were washed with water (1×50 ml)
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-07f2a65636c34157b1cbc20d11427bd8
Source dataset
uspto-grants-1987_03
Patent number
US04650810

Reaction notes

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