Diethanolamine → HCID 135462962, compound

HRID 1531668Notes

Reaction equation

HRID 1531668 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]([NH:29][C:30]3[N:35]=[C:34](Cl)[N:33]=[C:32]([Cl:37])[N:31]=3)=[CH:13][CH:14]=2)[CH:9]=1)(=[O:7])=[O:6])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[NH:44]([CH2:48][CH2:49][OH:50])[CH2:45][CH2:46][OH:47]>CC(C)=O.Cl>[CH:1]([O:4][S:5]([C:8]1[C:17]([N:18]=[N:19][C:20]2[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=2)=[C:16]([OH:28])[C:15]2[C:10](=[CH:11][C:12]([NH:29][C:30]3[N:35]=[C:34]([N:44]([CH2:48][CH2:49][OH:50])[CH2:45][CH2:46][OH:47])[N:33]=[C:32]([Cl:37])[N:31]=3)=[CH:13][CH:14]=2)[CH:9]=1)(=[O:6])=[O:7])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8113DiethanolamineHCID 10340Sodium CarbonateHCID 135484107HCID 135484107, compound

Product 1

HCID 135462962HCID 135462962, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolvent

Procedure

7-(4,6-Dichloro-[1,3,5]-triazin-2-ylamino)-4-hydroxy-3-(4-methoxy-phenylazo)-napthalene-2-sulfonic acid isopropyl ester (Example 7, 200 mg, 0.36 mmol) in acetone (3 mL) was stirred under nitrogen with sodium carbonate (38 mg, 0.36 mmol). Diethanolamine (35 μL, 40 mg, 0.36 mmol) was added to the stirred suspension, and the reaction mixture was allowed to stir 60 h. The reaction mixture was diluted with hydrochloric acid (3 mL, 1 N) and filtered. The solid was triturated in methanol/ether (1:3) for 1 h and filtered to provide the title compound (179 mg, 0.28 mmol, 79%) as a red solid: NMR (DMSO-d6): δ 16.28 (s, 1H), 10.61 (s, 1H), 8.45 (s, 1H ), 8.30 (d, J=9 Hz, 1H), 7.88 (m, 2H), 7.76 (d, J=9 Hz, 2H), 7.15 (d, J=9 Hz, 2H), 4.78 (m, 1H), 3.90 (m, 13H), 1.23 (d, J=6 Hz, 6H); Analytical HPLC: 87%.

Workup

  1. filtrationfiltered
  2. customThe solid was triturated in methanol/ether (1:3) for 1 h
  3. filtrationfiltered

Sources & evidence

ORD record
ord-8dd33e34d94f40c9bd32a461bf77aa54
Source dataset
uspto-grants-2001_03
Patent number
US06200963B1

Reaction notes

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