Trimethyl orthoformate → HCID 89501076, compound

HRID 1467791Notes

Reaction equation

HRID 1467791 reaction equation
[Cl:1][C:2]1[C:8]([F:9])=[CH:7][C:5]([NH2:6])=[C:4]([I:10])[CH:3]=1.[N-:11]=[N+:12]=[N-:13].[Na+].[CH:15](OC)(OC)OC>CC(O)=O>[Cl:1][C:2]1[C:8]([F:9])=[CH:7][C:5]([N:6]2[CH:15]=[N:13][N:12]=[N:11]2)=[C:4]([I:10])[CH:3]=1

Participants

5

Reactant 3

HCID 9005Trimethyl orthoformateHCID 33557Sodium AzideHCID 575389634-Chloro-5-fluoro-2-iodoaniline

Product 1

HCID 89501076HCID 89501076, compoundYield 872.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To Intermediate 5A (47 g, 17.3 mmol) in AcOH (470 mL) was added NaN3 (33.76 g, 51.9 mmol) and trimethyl orthoformate (56.8 mL, 51.9 mmol). After 30 h, the reaction was poured into ice H2O, the solids were filtered-off and washed with petroleum ether to afford 49 g Intermediate 5B. MS (ESI) m/z: 324.8 (M+H)+.

Workup

  1. washwashed with petroleum ether

Sources & evidence

ORD record
ord-315bc01d802d432799d85647964c41d2
Source dataset
uspto-grants-2015_04
Patent number
US09000172B2

Reaction notes

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