Sulfuric Acid → HCID 58721711, compound

HRID 1246805Notes

Reaction equation

HRID 1246805 reaction equation
[CH:1]([N:14]1[CH2:17][C:16]([NH:20][CH3:21])([C:18]#[N:19])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:22]S(O)(=O)=O>C(Cl)Cl>[CH:1]([N:14]1[CH2:17][C:16]([NH:20][CH3:21])([C:18]([NH2:19])=[O:22])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 219057751-(Diphenylmethyl)-3-(methylamino)-3-azetidinecarbonitrile

Product 1

HCID 58721711HCID 58721711, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A vigorously stirred solution of 1-benzhydryl-3-methylaminoazetidine-3-carbonitrile (I-(29A-7)a; 2.10 g, 7.57 mmol) in methylene chloride (25 ml) cooled in an ice bath was treated with H2SO4 (4.0 ml, 76 mmol), dropwise. After the reaction mixture was allowed to warm to room temperature and stir overnight, it was cooled in an ice bath and then carefully quenched with concentrated NH4OH to pH 11. The mixture was extracted with methylene chloride, the combined organic layers were dried (Na2SO4) and then concentrated, in vacuo, to afford I-(29A-7)b (1.2 g, 54%) as an off-white solid: +ES MS (M+1) 296.3; 1H NMR (400 MHz, CD3OD) δ 7.41 (d, J=7.5 Hz, 4H), 7.25 (t, J=7.5 Hz, 4H), 7.16 (t, J=7.1 Hz, 2H), 4.48 (s, 1H), 3.41 (d, J=8.7 Hz, 2H), 3.09 (d, J=8.7 Hz, 2H), 2.24 (s, 3H).

Workup

  1. temperatureit was cooled in an ice bath
  2. customcarefully quenched with concentrated NH4OH to pH 11
  3. extractionThe mixture was extracted with methylene chloride
  4. dry with materialthe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated, in vacuo
  6. customto afford I-(29A-7)b (1.2 g, 54%) as an off-white solid

Sources & evidence

ORD record
ord-57a4e4188082470c8d0117b1fb1561f3
Source dataset
uspto-grants-2006_10
Patent number
US07129239B2

Reaction notes

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