Ammonia → HCID 14791311, compound

Reaction equation

CC1C=CC(S([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16](S(C2C=CC(C)=CC=2)(=O)=O)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][N:24](S(C2C=CC(C)=CC=2)(=O)=O)[CH2:25][CH2:26][CH2:27][CH2:28][NH:29]S(C2C=CC(C)=CC=2)(=O)=O)(=O)=O)=CC=1.[NH4+].[Na].[Cl-].[NH4+].N>>[NH2:29][CH2:28][CH2:27][CH2:26][CH2:25][NH:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][NH:16][CH2:15][CH2:14][CH2:13][CH2:12][NH2:11]

Participants

Reactant 5

HCID 222Ammonia

HCID 223Ammonium

HCID 25517Ammonium Chloride

HCID 5360545Sodium2×

HCID 22989092HCID 22989092, compound

Product 1

HCID 14791311HCID 14791311, compound

Procedure

Mix 1,6,14,19-tetra[(4-methylphenyl)sulfonyl]-1,6,14,19-tetraazanonadecane (3.9 g, 4 mmol) in dry liquid ammonium (25 mL) at -40° C. Add small pieces of sodium until a permanent blue color remains. Discharge the excess sodium with saturated ammonium chloride. Allow the ammonia to evaporate spontaneously and partition the residue between ethyl acetate and water. Separate the organic phase, dry (MgSO4) and evaporate the solvent in vacuo. Purify by silica gel chromatography to give the title compound.