Potassium Carbonate → HCID 56981938, compound

HRID 917518Notes

Reaction equation

HRID 917518 reaction equation
[CH:1]([C:4]([NH:6][CH:7]1[CH2:12][CH2:11][CH:10](CNC(N)=S)[CH2:9][CH2:8]1)=[O:5])([CH3:3])[CH3:2].[C:18]([O-])([O-])=O.[K+].[K+].[C:24]([NH:32][C:33]([NH:35]CC1CCC(NC(C(C)C)=O)CC1)=[S:34])(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O.CO>[C:24]([N:32]([CH3:18])[C:33]([NH:35][CH:10]1[CH2:9][CH2:8][CH:7]([NH:6][C:4]([CH:1]([CH3:2])[CH3:3])=[O:5])[CH2:12][CH2:11]1)=[S:34])(=[O:31])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 22253971HCID 22253971, compoundHCID 22254060N-[4-(Isopropylformylamino)cyclohexyl]methylthiourea

Product 1

HCID 56981938HCID 56981938, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Similarly, N-Benzoyl-N′-[4-(2-methoxyethylformyl-amino)-cyclohexyl]methylthiourea was obtained: 100% yield, 378 (ESMS, MH+); 1H NMR (CDCl3) δ 10.85 (broad, 1H), 9.03 (broad, 1H), 8.18 & 8.08 (two s, 1H), 7.84 (d, 2H, J=7.9 Hz), 7.64 (m, 1H), 7.52 (d, 2H, J=7.8 Hz), 3.63-3.24 (m, 7H), 3.34 & 3.33 (two m, 3H), 2.03-1.13 (m, 9H). N-[4-(Isopropylformylamino)cyclohexyl]methylthiourea: K2CO3 (2 equivalents) in water was added to a solution of N-benzoyl-N′-[4-(isopropylformylamino)-cyclohexyl]methyl-thiourea 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 concentrated. The crude product was chromatographed to yield the desired product: 100% yield; 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 concentrated
  6. customThe crude product was chromatographed

Sources & evidence

ORD record
ord-b6d2423cedaf4e6f9ae86a052d39ecbc
Source dataset
uspto-grants-2007_09
Patent number
US07273880B2

Reaction notes

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