Water → HCID 22601875, compound

HRID 2308420Notes

Reaction equation

HRID 2308420 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:23]2[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=2)([C:16]2[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=2)[C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[N:30]1[C:37](Cl)=[N:36][C:34]([Cl:35])=[N:33][C:31]=1[Cl:32].C([O-])([O-])=O.[Na+].[Na+].O>CC(C)=O>[Cl:35][C:34]1[N:33]=[C:31]([Cl:32])[N:30]=[C:37]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]([C:16]3[CH:21]=[CH:20][C:19]([NH:22][C:37]4[N:36]=[C:34]([Cl:35])[N:33]=[C:31]([Cl:32])[N:30]=4)=[CH:18][CH:17]=3)([C:23]3[CH:28]=[CH:27][C:26]([NH:29][C:37]4[N:36]=[C:34]([Cl:35])[N:33]=[C:31]([Cl:32])[N:30]=4)=[CH:25][CH:24]=3)[C:9]3[CH:10]=[CH:11][C:12]([NH:15][C:37]4[N:36]=[C:34]([Cl:35])[N:33]=[C:31]([Cl:32])[N:30]=4)=[CH:13][CH:14]=3)=[CH:6][CH:7]=2)[N:36]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7954Cyanuric chlorideHCID 10340Sodium CarbonateHCID 11825069TETRAKIS(4-AMINOPHENYL)METHANE

Product 1

HCID 22601875HCID 22601875, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of tetrakis(4-aminophenyl)methane (4.57 grams, 12.0 mmol; prepared as described in Example C) in acetone (96 milliliters) was added dropwise at 0° C. to a stirred solution of cyanuric chloride (9.06 grams, 49.1 mmol; obtained from Aldrich Chemical Co., Milwaukee, Wis.) in acetone (144 milliliters). The resulting mixture was kept at 0° C. for 1 hour, treated with Na2CO3 (5.21 grams, 49.2 mmol), and poured into water (960 milliliters). The precipitate was separated by filtration, washed with water, and dried to give the tetrakis[4-[(2,4-dichloro-1,3,5-triazin-6-yl)amino]phenyl]methane (7.97 grams, 8.20 mmol, 68 percent yield) as a colorless solid: mp>310° C.; 1H NMR (400 MHz, DMSO-d6, 25° C.) δ7.18 (d, 8H, 3J=8.7 Hz), 7.55 (d, 8H, 3J=8.7 Hz), 11.18 (s, 4H); 13C NMR (75.4 MHz, DMSO-d6, 25° C.)δ64.1, 121.7, 131.7, 135.8, 143.8, 164.6, 169.7, 170.7; MS (FAB, 2-nitrobenzyl alcohol) m/e 969. Anal. Calcd for C37H20Cl8N16: C, 45.71; H, 2.07; N, 23.05. Found: C, 46.03; H, 2.09; N, 22.61.

Workup

  1. customThe precipitate was separated by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-4465acbfbd0e4e41b0a9c9eee2150b6d
Source dataset
uspto-grants-2004_12
Patent number
US06835833B2

Reaction notes

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