Hexamethylenediamine → HCID 88852782, compound

HRID 1472986Notes

Reaction equation

HRID 1472986 reaction equation
[C:1]1(=[O:8])[O:7][C:5](=[O:6])[CH2:4][O:3][CH2:2]1.[CH2:9]([CH2:14][CH2:15][NH2:16])[CH2:10][CH2:11][CH2:12][NH2:13]>CN(C)C=O>[C:5]([CH2:4][O:3][CH2:2][C:1]([NH:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:14][CH2:15][NH:16][C:5]([CH2:4][O:3][CH2:2][C:1]([OH:7])=[O:8])=[O:6])=[O:8])([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 16402HexamethylenediamineHCID 782321,4-Dioxane-2,6-dione

Product 1

HCID 88852782HCID 88852782, compoundYield 25.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of Diglycolic anhydride (30 g) in Dimethylformamide (85 ml) at 60° C. was added dropwise a solution of 1,6-Hexamethylene diamine (11.6 g) in Dimethylformamide (50 ml). The reaction mixture was stirred at the same temperature for 1 hour. The reaction mixture was cooled to 0° C. and maintained for 3 hours. The solid was filtered and washed with chloroform and dried to get pure {[6-(2-Carboxy methoxy-acetylamino)-hexylcarbamoyl]-methoxy}-acetic acid (9 g) as white powder with a melting point of 178-180° C. The compound was characterized by 1H NMR (DMSO-d6) δ1.25 (m, 2H, CH2), 1.55 (m, 2H, CH2), 2.80 (m, 2H, CH2), 3.90 (s, 4H, 2×CH2), 7.90 (bs, 1H, NH).

Workup

  1. temperaturemaintained for 3 hours
  2. filtrationThe solid was filtered
  3. washwashed with chloroform
  4. customdried

Sources & evidence

ORD record
ord-d11f534d528c48dba824a0dbbe6be792
Source dataset
uspto-grants-2015_04
Patent number
US09012677B2

Reaction notes

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