Methane → HCID 22218623, compound

HRID 1795479Notes

Reaction equation

HRID 1795479 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[NH2:6][CH2:7][CH2:8][CH2:9][NH:10][CH:11]1[CH2:16][CH2:15][CH:14]([NH:17][CH2:18][CH2:19][CH2:20][NH2:21])[CH2:13][CH2:12]1.O.C>C(OCC)(=O)C.CO>[OH2:3].[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[NH2:21][CH2:20][CH2:19][CH2:18][NH:17][CH:14]1[CH2:15][CH2:16][CH:11]([NH:10][CH2:9][CH2:8][CH2:7][NH2:6])[CH2:12][CH2:13]1

Participants

7

Reactant 4

HCID 297MethaneHCID 962WaterHCID 6395Methanesulfonic AcidHCID 9899398HCID 9899398, compound

Product 1

HCID 22218623HCID 22218623, compoundYield 67.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 350 mL of methanesulfonic acid in 1345 mL of ethyl acetate was added to a solution of 285.8 g of N,N′-bis(3-aminopropyl)cyclohexane-1,4-diamine (I) in 6880 mL of methanol. After stirring for 2 h, filtering, washing with ethanol and drying, 625 g of a crude solid were obtained. The solid was treated and stirred with water (5 mL per gram of solid) and activated charcoal for 2 h. After filtering off the charcoal, evaporating the water under vacuum, and drying at 40° C. until constant weight, 515 g (67.2%) of the title compound were obtained, with a melting point of 261-5° C. 1H-NMR spectrum (δ, ppm, DMSO-d6): 1.4 (m, 4H), 1.91 (m, 4H), 2.14 (m, 4H), 2.3 (s, 12H), 2.90 and 3.20 (m 10H), 8 (10 H). 13C-NMR spectrum (δ, ppm, DMSO-d6): 22.4 (cyclohexane CH2), 24.6 (CH2), 34.6 (CH2—NH2), 38.5 (acid CH3), 38.6 (acid CH3), 39.6 (CH2—NH), 52.9 (cyclohexane CH). IR spectrum (cm−1, KBr): 3440 (H2O), 2944, 2860 (aliphatic CH), 1195 (SO3). Elemental analysis (%): theory, C 30.48, H 7.30, N 8.88; found, C 30.79, H 7.04, N 8.88.

Workup

  1. filtrationfiltering
  2. washwashing with ethanol
  3. customdrying
  4. custom625 g of a crude solid were obtained
  5. additionThe solid was treated
  6. filtrationAfter filtering off the charcoal
  7. customevaporating the water under vacuum
  8. customdrying at 40° C. until constant weight

Sources & evidence

ORD record
ord-091e21336cbb456db41238b95728c48e
Source dataset
uspto-grants-2006_04
Patent number
US07026514B2

Reaction notes

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