Diisopropylethylamine → HCID 149434098, compound

HRID 873782Notes

Reaction equation

HRID 873782 reaction equation
[C:1]1([CH3:14])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1/[CH:9]=[CH:10]/[C:11]([OH:13])=O.C([N:18](C(C)C)CC)(C)C.N[N:25]([CH:33]=[NH:34])[C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29].O.ON1C2C=CC=CC=2N=N1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>CN(C)C=O.C(OCC)(=O)C>[NH:18]=[C:33]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[NH:34][C:11](=[O:13])/[CH:10]=[CH:9]/[C:2]1[C:1]([CH3:14])=[CH:6][C:5]([CH3:7])=[CH:4][C:3]=1[CH3:8]

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27960291-Hydroxybenzotriazole hydrateHCID 13720922110795-27-2HCID 86691067Tert-butyl amino(imino)methylcarbamate

Product 1

HCID 149434098HCID 149434098, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(2E)-3-Mesitylacrylic acid (8.0 g; 42 mmol), diisopropylethylamine (27.2 g; 210 mmol), tert-butyl amino(imino)methylcarbamate (8.03 g; 50 mmol), and 1-hydroxybenzotriazole monohydrate (7.73 g; 50 mmol) were dissolved in N,N-dimethylformamide (170 mL), 2-(1H)-benzotriazol-1-yl-1,1,3,3-tetramethyluronium hexafluorophosphate (19.2 g; 50 mmol) was added thereto, and the mixture was stirred for 20 hours at room temperature. To the reaction solution, ethyl acetate (500 mL) was added, and the mixture was washed with 10% aqueous citric acid solution, brine, saturated aqueous sodium bicarbonate solution, and then brine. The organic layer was dried over anhydrous magnesium sulfate and then distilled under reduced pressure, to give 13.9 g of the title compound (yield 100%) as an oil.

Workup

  1. washthe mixture was washed with 10% aqueous citric acid solution, brine, saturated aqueous sodium bicarbonate solution
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-805090cec0cf4641ab350cfe8dfaf7f7
Source dataset
uspto-grants-2015_03
Patent number
US08975411B2

Reaction notes

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