Trimethyl orthoformate → HCID 89501076, compound

HRID 515760Notes

Reaction equation

HRID 515760 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 water, then solid was filtered-off and washed with petroleum ether to afford 49 g of Intermediate 5B. MS (ESI) m/z: 324.8 (M+H)+.

Workup

  1. washwashed with petroleum ether

Sources & evidence

ORD record
ord-24f0ea663c26440e804d9b5d0c648cee
Source dataset
uspto-grants-2015_08
Patent number
US09108951B2

Reaction notes

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