Dimethylcarbamoyl Chloride → alpha-Diethylcarbamylthio-6-methoxy-2-naphthylacetic acid

HRID 1579843Notes

Reaction equation

HRID 1579843 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:42]=[CH:41][C:40]2[C:35](=[CH:36][CH:37]=[C:38]([O:43][CH3:44])[CH:39]=2)[CH:34]=1)[C:30]([OH:32])=[O:31])(=O)N.C(NC(SC(C1C=CC2C(=CC=C(OC)C=2)C=1)C(O)=O)=O)C.CN(C)C(SC(C1C=CC2C(=CC=C(OC)C=2)C=1)C(O)=O)=O>>[CH2:1]([N:3]([CH2:7][CH3:8])[C:4]([S:28][CH:29]([C:33]1[CH:42]=[CH:41][C:40]2[C:35](=[CH:36][CH:37]=[C:38]([O:43][CH3:44])[CH:39]=2)[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 21569102alpha-Carbamylthio-6-methoxy-2-naphthylacetic acidHCID 21569125alpha-Dimethylcarbamylthio-6-methoxy-2-naphthylacetic acidHCID 86732901alpha-Ethylcarbamylthio-6-methoxy-2-naphthylacetic acid

Product 1

HCID 21569122alpha-Diethylcarbamylthio-6-methoxy-2-naphthylacetic 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-6-methoxy-2-naphthylacetic acid, α-ethylcarbamylthio-6-methoxy-2-naphthylacetic acid or α-dimethylcarbamylthio-6-methoxy-2-naphthylacetic acid.

Workup

  1. customthe products prepared

Sources & evidence

ORD record
ord-223595e68bfe40c3bf6bc68e0ad04983
Source dataset
uspto-grants-1976_01
Patent number
US03931269

Reaction notes

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