Benzhydrylamine → HCID 18763447, compound

HRID 431392Notes

Reaction equation

HRID 431392 reaction equation
[NH2:1][CH:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][C:17]=1[N+:26]([O-:28])=[O:27].C(N(CC)CC)C>ClCCl>[C:9]1([CH:2]([NH:1][S:22]([C:19]2[CH:20]=[CH:21][C:16]([Cl:15])=[C:17]([N+:26]([O-:28])=[O:27])[CH:18]=2)(=[O:23])=[O:24])[C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 7036BenzhydrylamineHCID 7323Benzenesulfonyl chloride, 4-chloro-3-nitro-HCID 8471Triethylamine

Product 1

HCID 18763447HCID 18763447, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of aminodiphenylmethane (1.9 g, 11 mmol) and 4-chloro-3-nitrobenzenesulfonyl chloride (2.56 g, 10 mmol) in 75 mL of dichloromethane was added triethylamine (2 mL, 14.4 mmol). The solution was stirred for 16 h. The reaction mixture was washed successively with 1M HCl and brine. The organic layer was dried over MgSO4, filtered and evaporated. The resulting yellow solid was recrystallized from ethyl acetate/hexane to give 2.98 g of product in (74%) yield as pale yellow crystals: 1H NMR (400 MHz, CDCl3) δ5.34 (d, 1H, J=7.0 Hz), 5.73 (d, 1H, J=7.0 Hz), 7.11-7.14 (m, 4H), 7.23-7.26 (m, 6H), 7.43 (d, 1H, J=8.5 Hz), 7.67 (dd, 1H, J=2.0, 8.5 Hz), 7.93 (d, 1H, J=2.0 Hz).

Workup

  1. washThe reaction mixture was washed successively with 1M HCl and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe resulting yellow solid was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-5ed566ea161d4bb69161ce2db0bca6f2
Source dataset
uspto-grants-2003_12
Patent number
US06656971B2

Reaction notes

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