Sodium Azide → N-(3-amino-4-chloro-2-fluorobenzyl)pivalamide

HRID 59344Notes

Reaction equation

HRID 59344 reaction equation
[Cl:1][C:2]1[C:7](C(O)=O)=[C:6]([F:11])[C:5]([CH2:12][NH:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:4][CH:3]=1.[N-:20]=[N+]=[N-].[Na+]>S(=O)(=O)(O)O>[NH2:20][C:7]1[C:6]([F:11])=[C:5]([CH:4]=[CH:3][C:2]=1[Cl:1])[CH2:12][NH:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 584833746-Chloro-2-fluoro-3-(pivalamidomethyl)benzoic acid

Product 1

HCID 56839978N-(3-amino-4-chloro-2-fluorobenzyl)pivalamideYield 63.3%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 6-chloro-2-fluoro-3-(pivalamidomethyl)benzoic acid (step-5 of Intermediate-51, 1.0 g, 3.48 mmol) in conc. sulphuric acid (10.0 mL) was added sodium azide (0.271 g, 4.18 mmol). The reaction mass was stirred at 50-60° C. for 18 h. The reaction mass was quenched in ammonia solution (cold) and solid obtained was filtered and suck dried to afford 0.570 g of the product. 1H NMR (300 MHz, DMSO d6): δ 1.11 (s, 9H), 4.21 (d, J=5.7 Hz, 2H), 5.30 (s, 2H), 6.39 (t, J=7.8 Hz, 1H), 7.00 (d, J=8.4 Hz, 1H), 7.98 (m, 1H); MS (m/z): 259.12 (M+H+).

Workup

  1. customThe reaction mass was quenched in ammonia solution (cold)
  2. customsolid obtained
  3. filtrationwas filtered
  4. customsuck dried

Sources & evidence

ORD record
ord-8fd372cd36174bedbb815fd70d38f0ae
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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