Dimethylformamide → tert-butyl N-[N-[2-(2,4,6-trimethylphenyl)sulfanylacetyl]carbamimidoyl]carbamate

HRID 873779Notes

Reaction equation

HRID 873779 reaction equation
C1(C)C=C(C)C=C(C)C=1C[C:10](O)=[S:11].C(N([CH:20]([CH3:22])[CH3:21])CC)(C)C.N[N:24]([CH:32]=[NH:33])[C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28].[OH2:34].ON1C2[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=2N=N1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=[CH:60][C:55]=2N=N1.C[N:70](C)C=O>C(OCC)(=O)C>[NH:70]=[C:32]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[NH:33][C:55](=[O:34])[CH2:60][S:11][C:10]1[C:44]([CH3:39])=[CH:43][C:42]([CH3:41])=[CH:22][C:20]=1[CH3:21]

Participants

8

Reactant 6

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27960291-Hydroxybenzotriazole hydrateHCID 86691067Tert-butyl amino(imino)methylcarbamateHCID 178425024HCID 178425024, compound

Product 1

HCID 149434106tert-butyl N-[N-[2-(2,4,6-trimethylphenyl)sulfanylacetyl]carbamimidoyl]carbamateYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Mesitylthio acetic acid (6.90 g; 33 mmol), diisopropylethylamine (21.2 g; 164 mmol), tert-butyl amino(imino)methylcarbamate (6.37 g; 40 mmol), and 1-hydroxybenzotriazole monohydrate (6.13 g; 40 mmol) were dissolved in N,N-dimethylformamide (120 mL), 2-(1H)-benzotriazol-1-yl-1,1,3,3-tetramethyluronium hexafluorophosphate (15.2 g; 40 mmol) was added, and the mixture was stirred for 15 hours at room temperature. To the reaction solution, ethyl acetate (300 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 14.3 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-1b3643ce49254059b0188c9fe8546e72
Source dataset
uspto-grants-2015_03
Patent number
US08975411B2

Reaction notes

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