Chloroacetyl chloride → HCID 18402989, compound

HRID 1017178Notes

Reaction equation

HRID 1017178 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-0ff24905c1424263a416b63727de443b
Source dataset
uspto-grants-2002_11
Patent number
US06479435B1

Reaction notes

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