1,2-Dichloroethane → HCID 70169793, compound

HRID 716716Notes

Reaction equation

HRID 716716 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10][NH2:11])=[CH:4][CH:3]=1.[CH3:12][O:13][C:14]([CH:16]1[CH2:21][CH2:20][CH:19]([C:22](O)=[O:23])[CH2:18][CH2:17]1)=[O:15].C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.CCN(CC)CC>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][CH2:9][CH2:10][NH:11][C:22]([CH:19]2[CH2:18][CH2:17][CH:16]([C:14]([O:13][CH3:12])=[O:15])[CH2:21][CH2:20]2)=[O:23])=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 181649HOAtHCID 2968504-(Methoxycarbonyl)cyclohexane-1-carboxylic acidHCID 27941942-[(4-chlorophenyl)thio]ethanamine

Product 1

HCID 70169793HCID 70169793, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[(4-chlorophenyl)sulfanyl]ethanamine (12.2 g, 542 mmol) in DMF (350 ml) was added sequentially 4-(methoxycarbonyl)cyclohexanecarboxylic acid (cis/trans mixture), EDC (11.4 g, 59.7 mmol) and HOAt (1.48 g, 10.9 mmol) at room temperature followed by Et3N (17.39 ml, 125 mmol). The reaction was stirred overnight at ambient temperature, diluted with water and extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered and conc. The residue was purified by silica gel flash chromatography (0-70% EtOAc in heptane) to afford the product. LCMS: M+H=356.1.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. customconc. The residue was purified by silica gel flash chromatography (0-70% EtOAc in heptane)
  5. customto afford the product

Sources & evidence

ORD record
ord-2a5b8a0a5fa64efebd9af52f0ca9d72e
Source dataset
uspto-grants-2015_11
Patent number
US09193697B2

Reaction notes

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