2-Aminothiazole → N,N-Dicyclohexyl-N'-1,3-thiazol-2-yl-2-imidodicarbonic diamide

HRID 1673109Notes

Reaction equation

HRID 1673109 reaction equation
Cl[C:2]([N:4]=[C:5]=[O:6])=[O:3].[CH:7]1([NH:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.C(N(CC)CC)C.[NH2:27][C:28]1[S:29][CH:30]=[CH:31][N:32]=1>O1CCCC1>[CH:14]1([N:13]([CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[C:2]([NH:4][C:5]([NH:27][C:28]2[S:29][CH:30]=[CH:31][N:32]=2)=[O:6])=[O:3])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 7582DicyclohexylamineHCID 8471TriethylamineHCID 119708Isocyanatocarbonyl chloride

Product 1

HCID 16046747N,N-Dicyclohexyl-N'-1,3-thiazol-2-yl-2-imidodicarbonic diamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared as described in General Procedure 2. To chlorocarbonyl isocyanate (0.2 g) in tetrahydrofuran at −20-0° C. was added dicyclohexylamine (1 equivalent) and triethylamine (0.27 mL). After 20 min 2-aminothiazole (0.2 g) was added and the reaction allowed to warm to room temperature over 3 h and stirred overnight at room temperature. The reaction mixture was partially concentrated. The crude product was then dissolved in tetrahydrofuran and purified by flash chromatography (Eluant 20 dichloromethane:1 methanol).

Workup

  1. customPrepared
  2. concentrationThe reaction mixture was partially concentrated
  3. dissolutionThe crude product was then dissolved in tetrahydrofuran
  4. custompurified by flash chromatography (Eluant 20 dichloromethane:1 methanol)

Sources & evidence

ORD record
ord-4e11473f457a47d9a3d4a506a54ae6bd
Source dataset
uspto-grants-2011_08
Patent number
US07999114B2

Reaction notes

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