1,2-Dichloroethane → HCID 131728081, compound

HRID 2060144Notes

Reaction equation

HRID 2060144 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 (Preparation B10) (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-63c937515d2747e6a084614418474cce
Source dataset
uspto-grants-2012_10
Patent number
US08277807B2

Reaction notes

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