p-Chlorophenoxyacetyl chloride → HCID 66802536, compound

HRID 588749Notes

Reaction equation

HRID 588749 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[C:5]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)=[CH:9][S:8][C:6]=2[N:7]=1.C(N(CC)C(C)C)(C)C.[Cl:33][C:34]1[CH:44]=[CH:43][C:37]([O:38][CH2:39][C:40](Cl)=[O:41])=[CH:36][CH:35]=1>O1CCOCC1.ClCCl>[NH2:1][C:2]1[N:3]=[C:4]([N:18]2[CH2:23][CH2:22][N:21]([C:40](=[O:41])[CH2:39][O:38][C:37]3[CH:43]=[CH:44][C:34]([Cl:33])=[CH:35][CH:36]=3)[CH2:20][CH2:19]2)[C:5]2[C:10]([C:11]3[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=3)=[CH:9][S:8][C:6]=2[N:7]=1

Participants

6

Reactant 3

HCID 77771p-Chlorophenoxyacetyl chlorideHCID 81531DiisopropylethylamineHCID 71492232HCID 71492232, compound

Product 1

HCID 66802536HCID 66802536, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of Example 1 (135 mg, 0.41 mmol) in 1,4-dioxane (15 mL) were added N,N-diisopropylethylamine (169 μL, 1.02 mmol) and 4-chlorophenoxyacetyl chloride (0.45 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane and the organic layer was extracted several times with water. The combined organic layers were evaporated in vacuo and the crude residue was purified by silica gel flash chromatography, the mobile phase being a mixture of methanol and dichloromethane (in a ratio gradually ranging from 0.5% to 1% methanol in dichloromethane), yielding the title compound as a white powder. MS (m/z) 498 [M+H]+.

Workup

  1. extractionthe organic layer was extracted several times with water
  2. customThe combined organic layers were evaporated in vacuo
  3. customthe crude residue was purified by silica gel flash chromatography
  4. additiona mixture of methanol and dichloromethane (in a ratio

Sources & evidence

ORD record
ord-822e3bd1f139414fae95d0a29357e999
Source dataset
uspto-grants-2016_01
Patent number
US09227984B2

Reaction notes

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