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2,2-Dimethyl-1,3-dioxane-4,6-dione → Methyl 3-bromo-4-(((2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino)benzoate

HRID 1778262
Notes
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Reaction equation

HRID 1778262 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[Br:12].[CH3:13][C:14]1([CH3:22])[O:21][C:19](=[O:20])[CH2:18][C:16](=[O:17])[O:15]1.[CH:23](OCC)(OCC)OCC>C(O)(C)C>[Br:12][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:2]=1[NH:1][CH:23]=[C:18]1[C:19](=[O:20])[O:21][C:14]([CH3:22])([CH3:13])[O:15][C:16]1=[O:17])[C:6]([O:8][CH3:9])=[O:7]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 31214Ethyl orthoformateHCID 1515280Methyl 4-amino-3-bromobenzoate

Product 1

HCID 118323992Methyl 3-bromo-4-(((2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino)benzoate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of methyl 4-amino-3-bromobenzoate (2 g, 8.69 mmol) in isopropanol (10 mL) was added Meldrum's acid (1.63 g, 11 mmol) and triethyl orthoformate (5.26 mL, 31.6 mmol). The resulting mixture was heated at 100° C. for 4 hr and cooled to room temperature. The resulting precipitates were filtered off and washed with 10% Et2O/hexanes to yield methyl 3-bromo-4-(((2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino)benzoate. (M+Na)+: 408.

Workup

  1. temperaturecooled to room temperature
  2. customThe resulting precipitates
  3. filtrationwere filtered off
  4. washwashed with 10% Et2O/hexanes

Sources & evidence

ORD record
ord-e9a960eb02714e29a5292f082a2f145e
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09266835B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes