Diisopropylethylamine → HCID 90402445, compound

HRID 1854761Notes

Reaction equation

HRID 1854761 reaction equation
[CH3:1][C:2]([S:5](Cl)=[O:6])([CH3:4])[CH3:3].Cl.[NH2:9][C:10]1([C:13]#[N:14])[CH2:12][CH2:11]1.C(N(C(C)C)C(C)C)C>ClCCl.CN(C1C=CN=CC=1)C>[C:13]([C:10]1([NH:9][S:5]([C:2]([CH3:4])([CH3:3])[CH3:1])=[O:6])[CH2:12][CH2:11]1)#[N:14]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 46868612-Methylpropane-2-sulfinyl chlorideHCID 145863631-Amino-1-cyclopropanecarbonitrile hydrochloride

Product 1

HCID 90402445HCID 90402445, compoundYield 101.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

2-methylpropane-2-sulfinic chloride (1.0 ml, 8.4 mmol) was added to a stirring solution of 1-aminocyclopropanecarbonitrile hydrochloride (1 g, 8 mmol) in dichloromethane (21 ml) and N-ethyl-N-isopropylpropan-2-amine (3.0 ml, 17 mmol) at 0° C. DMAP (10 mg, 0.084 mmol) was added and the reaction was allowed to stir 2 h at rt. The mixture was diluted with dichloromethane and washed with sat NH4Cl aq, and sat NaCl aq. The organic phase was dried over Na2SO4, filtered and concentrated to give the expected product N-(1-cyanocyclopropyl)-2-methylpropane-2-sulfinamide (1.5 g, 8.1 mmol, 95% yield) as a sticky yellow solid consistent by LCMS. LC-MS retention time: 1.40 min; m/z (MH+): 187. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Phenomenex-Luna 3u C18 2.0×30 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 1 mL/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 2 min, a hold time of 1 min, and an analysis time of 3 min where solvent A was 5% MeOH/95% H2O/10 mM ammonium acetate and solvent B was 5% H2O/95% MeOH/10 mM ammonium acetate. MS data was determined using a Micromass Platform for LC in electrospray mode.

Workup

  1. washwashed
  2. dry with materialwas dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ef6aa007450c403a8fdced8a9df04a97
Source dataset
uspto-grants-2015_02
Patent number
US08962651B2

Reaction notes

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