Sulfuric Acid → HCID 58721711, compound

HRID 348014Notes

Reaction equation

HRID 348014 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-3A-2a; 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 aqueous 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-3A-2b (1.2 g, 54%) as an off-white solid: +ESI 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 aqueous 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-3A-2b (1.2 g, 54%) as an off-white solid

Sources & evidence

ORD record
ord-bcd5ba19e04144f4bcf253a59ee536c7
Source dataset
uspto-grants-2007_02
Patent number
US07176210B2

Reaction notes

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