Chloroacetyl chloride → HCID 22316553, compound

HRID 467908Notes

Reaction equation

HRID 467908 reaction equation
[NH2:1][C:2]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:13])=[O:5].[Cl:21][CH2:22][C:23](Cl)=O>C(O)(=O)C>[Cl:21][CH2:22][C:23]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[Cl:13])[C:4](=[O:5])[C:3]2[C:2](=[CH:17][C:16]([N+:18]([O-:20])=[O:19])=[CH:15][CH:14]=2)[N:1]=1

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 22316574HCID 22316574, compound

Product 1

HCID 22316553HCID 22316553, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Prepared according to Procedure B with 1o (500 mg, 1.71 mmol) and chloroacetyl chloride (0.41 mL, 5.14 mmol) in acetic acid (10 mL). Purified by extraction from aqueous K2CO3, followed by two chromatographies in CH2Cl2 to afford 338 mg of a yellow oil (56%). 1H NMR (CDCl3) δ: 8.64 (d, J=2.2 Hz, 1H); 8.48 (d, J=8.8 Hz, 1H); 8.32 (dd, J=2.2, 8.7 Hz, 1H); 7.66 (dd, J=2.5, 6.0 Hz, 1H); 7.52-7.59 (m, 3H); 4.41 (d, J=12 Hz, 1H), 4.10 (d, J=12 Hz, 1H). MS (ES): m/z 350.0 (M+).

Workup

  1. customPrepared
  2. customPurified by extraction from aqueous K2CO3

Sources & evidence

ORD record
ord-4cb98ea1821b442abc761f17d4d4b8a7
Source dataset
uspto-grants-2014_01
Patent number
US08623881B2

Reaction notes

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