Water → HCID 135987425, compound

HRID 841148Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=2[CH3:22])[N:12]=[C:11]([C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][C:24]=2[OH:30])[N:10]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:38]([CH3:44])[C:39]([O:41][CH2:42][CH3:43])=[O:40].O>CN(C)C=O>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=2[CH3:22])[N:12]=[C:11]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH:38]([C:39]([O:41][CH2:42][CH3:43])=[O:40])[CH3:44])=[CH:25][C:24]=2[OH:30])[N:10]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 37.9 g (0.100 mol) of 2,4-bis(2′,4′-dimethylphenyl)-6-(2′,4′-dihydroxyphenyl)-1,3,5-triazine, 14.5 g ( 0.105 mol) of potassium carbonate (Fluka, 99.0%) in 250 ml of N,N-dimethylformamide (DMF, Fluka, 99.5%) there are added dropwise with stirring at 80° C. 19.0 g (0.105 mol) of ethyl 2-bromopropionate (Fluka, 98%). The mixture is held at 80° C. for 1 h, then poured into 4 l of cold water and subjected to extraction with 2 l of ethyl acetate. The organic phase is filtered and washed with 2×500 ml of water and dried (MgSO4). Removal of the solvent and drying at 60° C./60 mmHg/24 h give 39.0 g of 2,4-bis(2′,4′-dimethylphenyl)-6-(2′-hydroxy-4′-(1″-(ethoxycarbonyl)ethoxy)phenyl)-1,3,5-triazine as pale yellow crystals of m.p. 120-122° C.

Workup

additionare added dropwise
extractionsubjected to extraction with 2 l of ethyl acetate
filtrationThe organic phase is filtered
washwashed with 2×500 ml of water
dry with materialdried (MgSO4)
customRemoval of the solvent
customdrying at 60° C./60 mmHg/24 h

Sources & evidence

ORD record: ord-c4a70bb33bf34af786e0e63ef697ff97
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06369267B1

Reaction notes

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