Potassium Carbonate → N-[4-(Isopropylformylamino)cyclohexyl]methylthiourea

HRID 324525Notes

Reaction equation

HRID 324525 reaction equation
C([O-])([O-])=O.[K+].[K+].C([NH:15][C:16]([NH:18][CH2:19][CH:20]1[CH2:25][CH2:24][CH:23]([NH:26][C:27]([CH:29]([CH3:31])[CH3:30])=[O:28])[CH2:22][CH2:21]1)=[S:17])(=O)C1C=CC=CC=1>O.CO>[CH:29]([C:27]([NH:26][CH:23]1[CH2:24][CH2:25][CH:20]([CH2:19][NH:18][C:16]([NH2:15])=[S:17])[CH2:21][CH2:22]1)=[O:28])([CH3:31])[CH3:30]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 22253971HCID 22253971, compound

Product 1

HCID 22254060N-[4-(Isopropylformylamino)cyclohexyl]methylthioureaYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

An aqueous solution of K2CO3 (2 equivalents) in water was added to a solution of N-benzoyl-N′-[4-(isopropylformylamino)cyclohexyl]methylthiourea in MeOH and stirred at room temperature overnight. The solvent was removed in vacuo and the residue was dissolved in EtOH. The solution was filtered to remove a white precipitate and the filtrate was concentrated. The crude product was chromatographed to yield the desired product: 100% yield; 258 (ESMS, MH+); 1H NMR (CD3OD) δ 8.15 & 8.13 (two s, 1H), 4.15 & 3.73 (two m, 1H), 3.34 & 2.97 (two m, 1H), 3.29 (m, 2H), 1.26 (d, 3H, J=6.7 Hz), 1.23(d, 3H, J=6.7 Hz), 1.91-1.03 (m, 9H).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in EtOH
  3. filtrationThe solution was filtered
  4. customto remove a white precipitate
  5. concentrationthe filtrate was concentrated
  6. customThe crude product was chromatographed

Sources & evidence

ORD record
ord-d53a051a815c4277ab621f48c9c7aab1
Source dataset
uspto-grants-2001_04
Patent number
US06218408B1

Reaction notes

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