Carbamic Acid → HCID 54221094, compound

HRID 442398Notes

Reaction equation

HRID 442398 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]12[CH2:10][CH:7]([CH2:8][CH2:9]1)[CH2:6][CH2:5]2.[C:11](=O)=[O:12].C(=O)(O)N>ClC1C=CC=CC=1>[N:1]([CH2:2][CH2:3][C:4]12[CH2:10][CH:7]([CH2:8][CH2:9]1)[CH2:6][CH2:5]2)=[C:11]=[O:12]

Participants

5

Reactant 3

HCID 277Carbamic AcidHCID 280Carbon DioxideHCID 21391864HCID 21391864, compound

Product 1

HCID 54221094HCID 54221094, compound

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

Following the procedure of Example 1 (Stage 3), 140 g (0.62 mol) 2-aminoethyl-2-(3-aminopropyl)5- (or 6) -aminoethyl-bicyclo-[2,2,1]-heptane in 1.5 liters of boiling chlorobenzene are initially converted with CO2 into the carbamic acid derivative which is thereafter phosgenated, first in the cold and then at boiling temperature. The 2-isocyanatomethyl-2-(3-isocyanatopropyl)-5- (or 6) -isocyanato ethyl-bicyclo-[2,2,1]-heptane is obtained from the clear reaction solution in the form of a pale yellow liquid by distillation at a boiling point of 186°-188° C./ 0.1 Torr. Yield 170 g (90%). Viscosity 80 cP/20° C.

Sources & evidence

ORD record
ord-b8546f920f664b158ebd174fefe7554d
Source dataset
uspto-grants-1977_08
Patent number
US04045462

Reaction notes

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