Chloroacetyl chloride → HCID 22316577, compound

HRID 241906Notes

Reaction equation

HRID 241906 reaction equation
[NH2:1][C:2]1[CH:17]=[C:16]([F:18])[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:19][CH2:20][C:21](Cl)=O>C(O)(=O)C>[Cl:19][CH2:20][C:21]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]([F:18])=[CH:15][CH:14]=2)[N:1]=1

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 22316582HCID 22316582, compound

Product 1

HCID 22316577HCID 22316577, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Prepared according to Procedure B with 1c (500 mg, 1.89 mmol) and chloroacetyl chloride (0.45 mL, 5.67 mmol) in acetic acid (10 mL). Purified by extraction from aqueous K2CO3 followed by recrystallization from isopropanol to afford 501 mg of a yellow crystalline solid (82%). 1H NMR (CDCl3) δ: 8.32 (dd, J=6.0, 8.9 Hz, 1H); 7.59-7.66 (m, 1H); 7.50-7.55 (m, 3H); 7.44 (dd, J=2.4, 9.4 Hz, 1H); 7.27 (dt, J=2.5, 8.5 Hz, 1H); 4.37 (d, J=12 Hz, 1H), 4.07 (d, J=12 Hz, 1H). MS (ES): m/z 323.0 (M+).

Workup

  1. customPrepared
  2. customPurified by extraction from aqueous K2CO3
  3. customfollowed by recrystallization from isopropanol

Sources & evidence

ORD record
ord-71a39c90a2dc4a7d88729ef50d4db545
Source dataset
uspto-grants-2014_02
Patent number
US08653077B2

Reaction notes

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