1,2-Dichloroethane → N-{4-[(diethylamino)sulfonyl]phenyl}-2,2-diphenylacetamide

HRID 2186773Notes

Reaction equation

HRID 2186773 reaction equation
[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([N:27]([CH2:30][CH3:31])[CH2:28][CH3:29])(=[O:26])=[O:25])=[CH:20][CH:19]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>ClCCl>[CH2:30]([N:27]([CH2:28][CH3:29])[S:24]([C:21]1[CH:22]=[CH:23][C:18]([NH:17][C:8](=[O:10])[CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:19][CH:20]=1)(=[O:26])=[O:25])[CH3:31]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 8333Diphenylacetic AcidHCID 757711-HydroxybenzotriazoleHCID 950674-amino-N,N-diethylbenzene-1-sulfonamide

Product 1

HCID 1010402N-{4-[(diethylamino)sulfonyl]phenyl}-2,2-diphenylacetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of diphenylacetic acid (223 mg, 1.05 mmol), 4-Amino-N,N-diethyl-benzenesulfonamide (240 mg, 1.05 mmol), HOBT (213 mg, 1.58 mmol), and EDC (242 mg, 1.26 mmol) in dichloromethane (20 mL) was stirred at 23° C. for 15 hours. The reaction mixture was washed with 1N aqueous sodium hydroxide (10 mL), 1N aqueous hydrochloric acid (10 mL), and saturated aqueous sodium chloride (10 mL). The organics were dried over magnesium sulfate and were concentrated. Flash chromatography (20% THF in hexanes grading to 40% THF in hexanes) provided the title compound as orange oil that solidified upon standing (224 mg). MS 423 (M+1)

Workup

  1. washThe reaction mixture was washed with 1N aqueous sodium hydroxide (10 mL), 1N aqueous hydrochloric acid (10 mL), and saturated aqueous sodium chloride (10 mL)
  2. dry with materialThe organics were dried over magnesium sulfate
  3. concentrationwere concentrated

Sources & evidence

ORD record
ord-f2ac421a6b9447968dede821e6bf1078
Source dataset
uspto-grants-2002_06
Patent number
US06407120B1

Reaction notes

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