1,2-Dichloroethane → HCID 131728081, compound

HRID 425192Notes

Reaction equation

HRID 425192 reaction equation
[CH2:1]([O:8]C1C=C(OCC2C=CC=CC=2)C(C(C)C)=CC=1C(O)=O)C1C=CC=CC=1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.C(N(CC)CC)C.[Cl:50][C:51]1[CH:52]=[C:53]2[C:57](=[CH:58][CH:59]=1)[CH2:56][NH:55][CH2:54]2>CN(C=O)C>[Cl:50][C:51]1[CH:52]=[C:53]2[C:57](=[CH:58][CH:59]=1)[CH2:56][N:55]([CH:1]=[O:8])[CH2:54]2

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 181649HOAtHCID 147958665-ChloroisoindolineHCID 591678792,4-Dibenzyloxy-5-isopropyl-benzoic acid

Product 1

HCID 131728081HCID 131728081, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2,4-bis-benzyloxy-5-isopropyl-benzoic acid (0.451 g, 1.2 mmol), EDC (0.276 mg, 1.44 mmol), HOAT (0.196 mg, 1.44 mmol), triethylamine (0.5 ml, 3.6 mmol) and 5-chloro-2,3-dihydro-1H-isoindole (0.187 g, 1.2 mmol) (Preparation C3) in DMF (5 ml) was stirred at room temperature for 16 hours, then evaporated under vacuum. The crude material was dissolved in ethyl acetate and extracted twice with saturated NaHCO3, organics washed with water three times, then evaporated under vacuum to give 0.5 g of 2,4-bis-benzyloxy-5-isopropyl-phenyl)-(5-chloro-1,3-dihydro-isoindol-2-yl)-methanone. MS: [M+H]+ 512.

Workup

  1. customevaporated under vacuum
  2. dissolutionThe crude material was dissolved in ethyl acetate
  3. extractionextracted twice with saturated NaHCO3
  4. washorganics washed with water three times
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-fba08210eeac444793423dfe588d3d53
Source dataset
uspto-grants-2012_01
Patent number
US08106057B2

Reaction notes

Loading…