Triphenylphosphine → Methyl 2-(4-methyl-1,1-dioxido-6-(2,4,6-trichlorophenyl)-1,2,6-thiadiazinan-2-yl)acetate

HRID 1522066Notes

Reaction equation

HRID 1522066 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][S:11]([NH:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])(=[O:13])=[O:12].[CH3:20][CH:21]([CH2:24]O)[CH2:22]O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>>[CH3:20][CH:21]1[CH2:24][N:10]([C:3]2[C:4]([Cl:9])=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[S:11](=[O:13])(=[O:12])[N:14]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH2:22]1

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 75103MethylpropanediolHCID 5363146Diisopropyl azodicarboxylateHCID 86708913Methyl 2-(N-(2,4,6-trichlorophenyl)sulfamoylamino)acetate

Product 1

HCID 86708915Methyl 2-(4-methyl-1,1-dioxido-6-(2,4,6-trichlorophenyl)-1,2,6-thiadiazinan-2-yl)acetateYield 69%

Procedure

To methyl 2-(N-(2,4,6-trichlorophenyl)sulfamoylamino)acetate (3.0 g, 8.3 mmol), 2-methylpropan-1,3-diol (1.18 mL, 8.3 mmol) and PPh3 (5.4 g, 20.7 mmol), was dropwisely added DIAD (4 mL, 20.7 mmol) with adjustment of external temperature to 0° C. The reaction mixture was agitated for 3 hr at room temperature, extracted with EtOAc, dried (Na2SO4), filtered and concentrated under reduced pressure, followed by column chromatography (MeOH/DCM 1%), finally giving the title compound (2.3 g, y=65%, solid). 1H NMR (300 MHz, CDCl3): δ 7.41 (d, J=2.4 Hz, 1H), 7.37 (d, J=2.4 Hz, 1H), 4.44 (d, J=17 Hz, 1H), 4.37-3.86 (m, 5H), 3.59-3.41 (m, 1H), 3.38-3.13 (m, 1H), 2.75-2.53 (m, 1H), 1.32 (t, J=7.1 Hz, 3H), 0.94 (t, J=7.1 Hz, 3H).

Workup

  1. customto 0° C
  2. extractionextracted with EtOAc
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f4ed5050a0f14eb69c85dd2281faf49a
Source dataset
uspto-grants-2015_07
Patent number
US09073906B2

Reaction notes

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