Dimethylcarbamoyl Chloride → alpha-Diethylcarbamylthio-3-chloro-4-cyclohexylphenylacetic acid

HRID 1576250Notes

Reaction equation

HRID 1576250 reaction equation
[CH2:1]([N:3]([CH2:7][CH3:8])[C:4](Cl)=[O:5])[CH3:2].C(Cl)(=O)N.C(NC(Cl)=O)C.CN(C)C(Cl)=O.C([S:28][CH:29]([C:33]1[CH:38]=[CH:37][C:36]([CH:39]2[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]2)=[C:35]([Cl:45])[CH:34]=1)[C:30]([OH:32])=[O:31])(=O)N.C(NC(SC(C1C=CC(C2CCCCC2)=C(Cl)C=1)C(O)=O)=O)C.CN(C)C(SC(C1C=CC(C2CCCCC2)=C(Cl)C=1)C(O)=O)=O>>[CH2:1]([N:3]([CH2:7][CH3:8])[C:4]([S:28][CH:29]([C:33]1[CH:38]=[CH:37][C:36]([CH:39]2[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44]2)=[C:35]([Cl:45])[CH:34]=1)[C:30]([OH:32])=[O:31])=[O:5])[CH3:2]

Participants

8

Reactant 7

HCID 6598Dimethylcarbamoyl ChlorideHCID 6916Diethylcarbamoyl chlorideHCID 68048Carbamic chlorideHCID 12321963N-ethylcarbamoyl chlorideHCID 21514611alpha-Dimethylcarbamylthio-3-chloro-4-cyclohexylphenylacetic acidHCID 21514616alpha-Carbamylthio-3-chloro-4-cyclohexylphenylacetic acidHCID 86733940alpha-Ethylcarbamylthio-3-chloro-4-cyclohexylphenylacetic acid

Product 1

HCID 21514613alpha-Diethylcarbamylthio-3-chloro-4-cyclohexylphenylacetic acid

Procedure

When diethylcarbamylchloride is replaced in the above procedure by carbamyl chloride (prepared in situ from potassium cyanate and anhydrous hydrogen chloride in anhydrous chloroform), ethylcarbamyl chloride or dimethylcarbamyl chloride, then the products prepared are α-carbamylthio-3-chloro-4-cyclohexylphenylacetic acid, α-ethylcarbamylthio-3-chloro-4-cyclohexylphenylacetic acid or α-dimethylcarbamylthio-3-chloro-4-cyclohexylphenylacetic acid.

Workup

  1. customthe products prepared

Sources & evidence

ORD record
ord-92c1e3e7e8c844cd84ce9c0ca68eed92
Source dataset
uspto-grants-1976_09
Patent number
US03979428

Reaction notes

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