Chloroacetyl chloride → HCID 18402989, compound

HRID 380300Notes

Reaction equation

HRID 380300 reaction equation
[NH2:1][C:2]1[C:3]([F:20])=[CH:4][C:5]([Cl:19])=[C:6]([CH:18]=1)[O:7][C:8]1[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:11]=[CH:10][N:9]=1.C(N(CC)CC)C.[Cl:28][CH2:29][C:30](Cl)=[O:31]>C1(C)C=CC=CC=1.C(Cl)Cl>[Cl:19][C:5]1[C:6]([O:7][C:8]2[C:13]([C:14]([F:17])([F:15])[F:16])=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:18][C:2]([NH:1][C:30](=[O:31])[CH2:29][Cl:28])=[C:3]([F:20])[CH:4]=1

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 18402965HCID 18402965, compound

Product 1

HCID 18402989HCID 18402989, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(5-amino-2-chloro-4-fluorophenoxy)-3-trifluoromethylpyridine (1.32 g) and triethylamine (0.8 ml) in toluene (20 ml) was stirred at 0° C. while a solution of chloroacetyl chloride (0.4 ml) in toluene (10 ml) was added. The mixture was stirred over night at room temperature and processed. Column chromatography on silica gel using methylene chloride as eluent gave a white solid (1.4 g), mp 146-9° C. 1H NMR (CDCl3, TMS): 4.20(2H, s), 7.12(1H, dd, J=5,8 Hz), 7.30(1H, d, J=9 Hz), 8.01(1H, m), 8.22(1H, m), 8.34(1H, d, J=7 Hz).

Workup

  1. additionwas added

Sources & evidence

ORD record
ord-1f0867a03d5f4ca080b0fa3c7e4d0a32
Source dataset
uspto-grants-2001_10
Patent number
US06303543B1

Reaction notes

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