Chloroacetyl chloride → HCID 22316555, compound

HRID 433255Notes

Reaction equation

HRID 433255 reaction equation
[NH2:1][C:2]1[CH:17]=[C:16]([F:18])[C:15]([F:19])=[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:20][CH2:21][C:22](Cl)=O>C(O)(=O)C>[Cl:20][CH2:21][C:22]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])=[C:15]([F:19])[CH:14]=2)[N:1]=1

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 22316576HCID 22316576, compound

Product 1

HCID 22316555HCID 22316555, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Prepared according to Procedure B with 1q (700 mg, 2.48 mmol) and chloroacetyl chloride (0.60 mL, 7.43 mmol) in acetic acid (12 mL). Purified by chromatography in CH2Cl2, followed by recrystallization from isopropanol to afford 219 mg of a yellow crystalline solid (26%). 1H NMR (CDCl3) δ: 8.07 (dd, J=8.5, 9.7 Hz, 1H); 7.64 (dd, J=2.5, 5.6 Hz, 1H); 7.60 (dd, J=3.5, 11 Hz, 1H); 7.55 (q, J=2.9 Hz, 3H); 7.52 (d, J=1.9 Hz, 1H); 7.49-7.51 (m, 1H); 4.36 (d, J=12 Hz, 1H), 4.06 (d, J=12 Hz, 1H). MS (ES): m/z 341.0 (M+).

Workup

  1. customPrepared
  2. customPurified by chromatography in CH2Cl2
  3. customfollowed by recrystallization from isopropanol

Sources & evidence

ORD record
ord-9697cf34163d4e138bbe38ea4cb2dc96
Source dataset
uspto-grants-2003_12
Patent number
US06667300B2

Reaction notes

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