Phosphoric Acid → Methyl (3-{[(methoxycarbonyl)amino]methyl}-3,5,5-trimethylcyclohexyl)carbamate

HRID 846831

Reaction equation

HRID 846831 reaction equation
P(=O)(O)(O)O.[NH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].[CH3:12][C:13]1([CH3:23])[CH2:18][C:17]([CH2:20][NH2:21])([CH3:19])[CH2:16][CH:15](N)[CH2:14]1>>[CH3:10][O:9][C:7]([NH:21][CH2:20][C:17]1([CH3:19])[CH2:18][C:13]([CH3:23])([CH3:12])[CH2:14][CH:15]([NH:6][C:7]([O:9][CH3:10])=[O:8])[CH2:16]1)=[O:8].[C:7](=[O:8])([OH:9])[NH2:6].[C:7](=[O:8])([OH:9])[NH2:6].[O:9]=[C:10]1[CH2:11][C:17]([CH3:19])([CH3:16])[CH2:18][C:13]([CH3:14])=[CH:12]1

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 5641Carbamic acid, ethyl esterHCID 17857Isophorone diamine

Product 2

HCID 3246761Methyl (3-{[(methoxycarbonyl)amino]methyl}-3,5,5-trimethylcyclohexyl)carbamateHCID 67742695HCID 67742695, compound

Procedure

After the completion of the feeding, the reaction mixture was aged at that temperature for 3 hours, neutralized with phosphoric acid and analyzed by gas chromatography. It was ascertained that a urethane compound corresponding to isophoronediamine, i.e., 3-methoxycarbonylaminomethyl-3,5,5-trimethyl-1-methoxycarbonylaminocyclohexane (abbreviated to "isophorone dicarbamate" or "IPDC") was obtained in a yield of 99% based on the isophorondiamine and in a yield of 99% based on the consumed dimethyl carbonate.

Sources & evidence

ORD record
ord-55ffec649ddc427eab095d06f0d63628
Source dataset
uspto-grants-1992_08
Patent number
US05138015

Linked notes

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