Trimethyl orthoformate → HCID 89501076, compound

HRID 1054124Notes

Reaction equation

HRID 1054124 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-fb061aeadbe84422b847152b73f61d7c
Source dataset
uspto-grants-2016_07
Patent number
US09394276B2

Reaction notes

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