1,2-Dichloroethane → HCID 57656042, compound

HRID 911625Notes

Reaction equation

HRID 911625 reaction equation
[CH:1]1([NH2:8])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.C(N(C(C)C)CC)(C)C.[C:32]([C:34]1[CH:42]=[CH:41][C:37]([C:38](O)=[O:39])=[C:36]([CH3:43])[CH:35]=1)#[N:33]>ClCCl>[C:32]([C:34]1[CH:42]=[CH:41][C:37]([C:38]([NH:8][CH:1]2[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:39])=[C:36]([CH3:43])[CH:35]=1)#[N:33]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 2899CycloheptylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 118193394-Cyano-2-methylbenzoic acid

Product 1

HCID 57656042HCID 57656042, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add cycloheptylamine (0.83 mL, 6.5 mmol), HOBT (838 mg, 6.2 mmol), EDC (1.2 g, 6.2 mmol) and diisopropylethylamine (3.2 mL, 18.6 mmol) to a solution of 4-cyano-2-methyl-benzoic acid (1 g, 6.2 mmol) in dichloromethane (20 mL) at room temperature under a nitrogen atmosphere. Stir the mixture for 16 h at room temperature. Wash the mixture with water (20 mL), separate and concentrate the organic layer in vacuo. Purify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (19:1 to 3:2 gradient) to obtain the desired intermediate (830 mg, 52%). MS (ES+) m/z: 257.3 (M+H)+.

Workup

  1. washWash the mixture with water (20 mL)
  2. customseparate
  3. concentrationconcentrate the organic layer in vacuo
  4. customPurify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (19:1 to 3:2 gradient)

Sources & evidence

ORD record
ord-ce59dc9d95494bc6b6cc35141d3d8c7b
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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