Cyanuric chloride → HCID 135484107, compound

HRID 1531667Notes

Reaction equation

HRID 1531667 reaction equation
[CH:1]([O:4][S:5]([C:8]1[C:17]([N:18]=[N:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)=[C:16]([OH:28])[C:15]2[C:10](=[CH:11][C:12]([NH2:29])=[CH:13][CH:14]=2)[CH:9]=1)(=[O:7])=[O:6])([CH3:3])[CH3:2].[N:30]1[C:37]([Cl:38])=[N:36][C:34](Cl)=[N:33][C:31]=1[Cl:32].C(=O)(O)[O-].[Na+]>CC(C)=O>[CH:1]([O:4][S:5]([C:8]1[C:17]([N:18]=[N:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)=[C:16]([OH:28])[C:15]2[C:10](=[CH:11][C:12]([NH:29][C:34]3[N:36]=[C:37]([Cl:38])[N:30]=[C:31]([Cl:32])[N:33]=3)=[CH:13][CH:14]=2)[CH:9]=1)(=[O:6])=[O:7])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 7954Cyanuric chlorideHCID 516892Sodium BicarbonateHCID 135494401HCID 135494401, compound

Product 1

HCID 135484107HCID 135484107, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

7-Amino-4-hydroxy-3-(4-methoxy-phenylazo)-napthalene-2-sulfonic acid isopropyl ester Example 6, 10 g, 24 mmol) was suspended in acetone (120 mL) and cyanuric chloride (6.65 g, 36 mmol) was added. Saturated sodium bicarbonate (3 mL) was then added to the suspension. After 3 h, the reaction mixture was filtered, to provide the title compound (11.1 g, 19.7 mmol, 82%) as a red solid: NMR (DMSO-d6): δ 16.30 (s, 1H), 11.86 (s, 1H), 8.25 (d, J=9 Hz, 1H), 8.08 (s, 1H), 7.96 (d, J=9 Hz, 1H), 7.87 (s, 1H), 7.76 (d, J=9 Hz, 2H), 7.15 (d, J=9 Hz, 2H), 4.61 (m, 1H), 3.92 (s, 3H), 1.31 (d, J=3 Hz, 6H); MS (° FAB): 2 chlorine isotope pattern, [M+Na+] 585, [M+H+] 563; Anal. Calc. for C23H20Cl2N6O5S: C, 49.03, H, 3.58, N, 14.92. Found: C, 47.66, H, 3.29, N, 14.31.

Workup

  1. filtrationthe reaction mixture was filtered

Sources & evidence

ORD record
ord-def119f3f5e84694b9d21df462688921
Source dataset
uspto-grants-2001_03
Patent number
US06200963B1

Reaction notes

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