Acetone Cyanohydrin → HCID 66747563, compound

HRID 2402151Notes

Reaction equation

HRID 2402151 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:5][C:6]1[N:7]=[C:8]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[S:9][C:10]=1[CH2:11]O.CC(C)(O)[C:25]#[N:26].N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(P(CCCC)CCCC)CCC>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:5][C:6]1[N:7]=[C:8]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[S:9][C:10]=1[CH2:11][C:25]#[N:26]

Participants

6

Reactant 4

HCID 6406Acetone CyanohydrinHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 66749674HCID 66749674, compound

Product 1

HCID 66747563HCID 66747563, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4-(3,4-dichlorobenzyl)-2-morpholinothiazol-5-yl)methanol (1.19 g, 3.31 mmol) in THF (58.6 mL) was added acetone cyanohydrin (0.454 mL, 4.97 mmol), 1,1′-(azodicarbonyl)dipiperidine (1.67 g, 6.62 mmol) and tributylphosphine (1.65 mL, 6.62 mmol) and the reaction was stirred for 3 hours at room temperature. The reaction was concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate/DCM=0/100→20/80) to give 551 mg (45% yield) of the title compound as a beige solid. LC/MS (FA) ES+ 368, 370. NMR (400 MHz, CDCl3) δ: 7.35 (d, 1H, J=6.0 Hz), 7.32 (d, 1H, J=2.0 Hz), 7.07 (dd, 1H, J=6.0, 2.0 Hz), 3.82 (s, 2H), 3.80-3.77 (m, 4H), 3.66 (s, 2H), 3.42-3.40 (m, 4H).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customThe residue was purified by silica gel chromatography (ethyl acetate/DCM=0/100→20/80)

Sources & evidence

ORD record
ord-006e3f34cf3146119efd0f2f816ba505
Source dataset
uspto-grants-2014_08
Patent number
US08796271B2

Reaction notes

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