1,2-Dichloroethane → HCID 10109962, compound

HRID 1182473Notes

Reaction equation

HRID 1182473 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=O)=[O:12].[CH:22]1[CH:23]=[CH:24][C:25]2[N:30](O)N=[N:28][C:26]=2[CH:27]=1.C(Cl)CCl.C1(N)C=CC=CC=1N>CN(C=O)C>[NH2:28][C:26]1[CH:27]=[CH:22][CH:23]=[CH:24][C:25]=1[NH:30][C:19](=[O:21])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:11]([C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)=[O:12]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 7243O-PhenylenediamineHCID 757711-HydroxybenzotriazoleHCID 109459918-(2-NAPHTHYL)-8-OXOOCTANOIC ACID

Product 1

HCID 10109962HCID 10109962, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-(2-naphthoyl)heptanoic acid 50 g (1.00 g, 3.52 mmol) in DMF (15 mL) were added HOBT (950 mg, 7.04 mmol) and EDC (1.00 g, 5.28 mmol). The mixture was stirred at room temperature for 1 hour, after which 1,2-phenylenediamine (760 mg, 7.04 mmol) was added and the solution was stirred at room temperature for 16 hours. The DMF was evaporated under high vacuum, deionized water was added, and the mixture was extracted with ethyl acetate (2×30 mL). The combined organic layers were washed with saturated sodium bicarbonate (20 mL), washed with brine (20 mL), and dried (MgSO4). The solvents were removed in vacuo and the title compound 63 (558 mg, 42%) was isolated by recrystallization from acetone and dichloromethane. 1H NMR (300 MHz, 20% CD3OD in CDCl3): δ 8.47 (s, 1H), 8.10-7.85 (m, 4H), 7.63-7.50 (m, 2H), 7.14-6.70 (m, 4H), 3.11 (t, J=7.2 Hz, 2H), 2.39 (t, J=7.5 Hz, 2H), 1.77 (m, 4H), 1.46 (m, 4H). 13C NMR (75 MHz, 20% CD3OD in CDCl3): δ 23.99, 25.40, 28.66, 28.74, 36.08, 38.23, 117.69, 119.09, 123.45, 124.01, 125.34, 126.53 126.86, 127.45, 128.19, 128.23, 129.28, 129.56, 132.23, 133.85, 135.32, 140.58, 172.81, 201.11.

Workup

  1. stirringthe solution was stirred at room temperature for 16 hours
  2. customThe DMF was evaporated under high vacuum
  3. additionwas added
  4. extractionthe mixture was extracted with ethyl acetate (2×30 mL)
  5. washThe combined organic layers were washed with saturated sodium bicarbonate (20 mL)
  6. washwashed with brine (20 mL)
  7. dry with materialdried (MgSO4)
  8. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-2fa65f7cbfe84386a3a862d490b47865
Source dataset
uspto-grants-2007_10
Patent number
US07288567B2

Reaction notes

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