1,2-Dichloroethane → HCID 11818464, compound

HRID 1246259Notes

Reaction equation

HRID 1246259 reaction equation
[CH3:1][S:2]([NH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=O)(=[O:4])=[O:3].[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(Cl)CCl>CN(C1C=CN=CC=1)C.C1COCC1>[C:15]1([NH:14][C:11](=[O:13])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][NH:5][S:2]([CH3:1])(=[O:3])=[O:4])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 6115AnilineHCID 3125359HCID 3125359, compound

Product 1

HCID 11818464HCID 11818464, compoundYield 95.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of acid 69 (100 mg, 0.48 mmol), aniline (60 μL, 0.66 mmol), and DMAP (5 mg) in THF (5 mL) was added EDC (119 mg, 0.57 mmol). The reaction mixture was stirred overnight, then partitioned between H2O (10 mL) and EtOAc (15 mL). The layers were separated, and the aqueous portion extracted with EtOAc (3×10 mL). The organic fractions were combined, washed with sat. NH4Cl (5 mL), then brine, dried over MgSO4, and filtered. Concentration under reduced pressure gave 70 as a white crystalline solid (130 mg, 0.46 mmol, 95%). 1H-NMR (400 MHz, DMSO-d6) δ 9.84 (s, 1H), 7.57 (d, 2H), 7.26 (t, 2H), 7.00 (t, 1H), 6.92 (t, 1H), 2.91 (dt, 2H), 2.85 (s, 3H), 1.58 (m, 2H), 1.47 (m, 2H), 1.31 (m, 2H).

Workup

  1. custompartitioned between H2O (10 mL) and EtOAc (15 mL)
  2. customThe layers were separated
  3. extractionthe aqueous portion extracted with EtOAc (3×10 mL)
  4. washwashed with sat. NH4Cl (5 mL)
  5. dry with materialbrine, dried over MgSO4
  6. filtrationfiltered
  7. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-dbd98b1332d74c8ca7d7536b513e155c
Source dataset
uspto-grants-2006_10
Patent number
US07126001B2

Reaction notes

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