2,2-Dimethyl-1,3-dioxane-4,6-dione → HCID 21873810, compound

HRID 639014Notes

Reaction equation

HRID 639014 reaction equation
[Br:1][C:2]1[C:3]([NH2:12])=[CH:4][C:5]2[O:10][CH2:9][CH2:8][O:7][C:6]=2[CH:11]=1.[CH:13](OCC)(OCC)OCC.[CH3:23][C:24]1([CH3:32])[O:29][C:28](=[O:30])[CH2:27][C:26](=[O:31])[O:25]1>C(O)C>[Br:1][C:2]1[C:3]([NH:12][CH:13]=[C:27]2[C:28](=[O:30])[O:29][C:24]([CH3:32])([CH3:23])[O:25][C:26]2=[O:31])=[CH:4][C:5]2[O:10][CH2:9][CH2:8][O:7][C:6]=2[CH:11]=1

Participants

5

Reactant 3

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 31214Ethyl orthoformateHCID 49832297-bromo-2,3-dihydro-1,4-benzodioxin-6-amine

Product 1

HCID 21873810HCID 21873810, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 7-Bromo-2,3-dihydro-benzo[1,4]dioxin-6-ylamine (14.8 g, 64.3 mmol, 1 eq), triethyl orthoformate (12.7 cm3, 77.2 mmol, 1.2 eq) and 2,2-dimethyl-[1,3]dioxane-4,6-dione (Meldrum's acid) (11.1 g, 77.2 mmol, 1.2 eq) in ethanol (70 mL) was heated to reflux. After 1 hour the mixture was allowed to cool to room temperature then filtered, washing with ethanol then ether, to afford a white solid (22.9 g, 93%). LC/MS (ES) m/z 384 (MH+ 100%); 1H-NMR (400 MHz, d4-DMSO), 11.43 (1H, br d, J=20, NH), 8.6 (1H, d, J=12, NCH═C), 7.49 (1H, s, CHCBr), 7.28 (1H, s, CHCN), 4.30-4.27 (4H, m, 2×(CH2O)), 1.68 (6H, s, (CH3)2C)

Workup

  1. temperaturewas heated to reflux
  2. filtrationthen filtered
  3. washwashing with ethanol

Sources & evidence

ORD record
ord-5ade6f98e1e341eca84856dfccdeaf8f
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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