1,2-Dichloroethane → HCID 178523569, compound

HRID 392656Notes

Reaction equation

HRID 392656 reaction equation
C(Cl)CCl.[C-:5]1([C:10]([OH:12])=O)[CH:9]=[CH:8][CH:7]=[CH:6]1.[CH-:13]1[CH:17]=[CH:16][CH:15]=[CH:14]1.[Fe+2:18].ON1C(=O)CCC1=O.[Cl-].[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[S:34][S:35][CH2:36][CH2:37][NH3+:38].CCN(CC)CC>C(Cl)Cl>[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[S:34][S:35][CH2:36][CH2:37][NH:38][C:10]([C:5]1[CH-:6][CH:7]=[CH:8][CH:9]=1)=[O:12].[CH-:13]1[CH:17]=[CH:16][CH:15]=[CH:14]1.[Fe+2:18]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 80170N-HydroxysuccinimideHCID 157642301271-42-7HCID 137937446HCID 137937446, compound

Product 1

HCID 178523569HCID 178523569, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

EDC (213 mg, 1.1 mmol) was added to a solution of ferrocenecarboxylic acid (232 mg, 1.0 mmol) and N-hydroxysuccinimide (128 mg, 1.1 mmol) dissolved in 20 mL of CH2Cl2. The solution was stirred at room temperature for 5 h and concentrated. The crude residue was dissolved in 8 mL of DMF and 2-(pyridin-2-yldisulfanyl)-ethyl-ammonium chloride (222 mg, 1.0 mmol) was added followed by Et3N (0.14 mL, 1.0 mmol). After stirring for 48 h, the solvent was evaporated in vacuo. The crude residue was purified by flash chromatography (gradient: hexanes/EtOAc, 1:1, v/v to EtOAc) to afford 113 mg (28% over 2 steps) of 12. 1H NMR 400 MHz (CDCl3) d 8.56 (m, 1H), 7.61 (m, 1H), 7.52 (m, 1H), 7.43 (t, J=6.8 Hz, 1H), 7.15 (m, 1H), 4.75 (m, 2H), 4.34 (m, 2H), 4.20 (s, 5H), 3.63 (q, J=6.0 HZ, 2H), 2.98 (t, J=6.0 Hz, 2H).

Workup

  1. concentrationconcentrated
  2. dissolutionThe crude residue was dissolved in 8 mL of DMF
  3. stirringAfter stirring for 48 h
  4. customthe solvent was evaporated in vacuo
  5. customThe crude residue was purified by flash chromatography (gradient: hexanes/EtOAc, 1:1, v/v to EtOAc)

Sources & evidence

ORD record
ord-92f18c6dd8ff445cbb06e2f3b96cc001
Source dataset
uspto-grants-2004_10
Patent number
US06803205B2

Reaction notes

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