Chloroacetyl chloride → HCID 54334577, compound

HRID 1003145Notes

Reaction equation

HRID 1003145 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=1.C(N(CC)CC)C.[Cl:30][CH2:31][C:32](Cl)=[O:33]>C(Cl)(Cl)Cl>[CH3:20][O:19][C:17](=[O:18])[C:16]1[CH:21]=[CH:22][C:13]([O:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:32](=[O:33])[CH2:31][Cl:30])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 18795323HCID 18795323, compound

Product 1

HCID 54334577HCID 54334577, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

The crude product from (iii) above (5.62 g, 18.84 mmol) and triethylamine (2.6 mL, 18.7 mmol) were dissolved in chloroform (90 mL) and cooled in an ice bath. A solution of chloroacetyl chloride (1.5 mL) in chloroform (40 mL) was added dropwise with stirring. After the completion of the addition, the solution was stirred in the ice bath for 15 minutes and warmed to ambient temperature and stirred for 20 hours. The solution was washed with water (4×80 mL). Drying (MgSO4) and concentration yielded the product (6.71 g, 93%) which was used without further purification. 1H NMR (CDCl3, δ): 7.95 (d), 6.87 (d), 6.54 s, br), 4.01 (d), 3.96 (t), 3.86 (s), 3.28 (q), 1.76 (m), 1.55 (m), 1.45 (m), 1.29 (m). 13C NMR (CDCl3, δ): 130.71, 130.66, 121.52, 113.23, 75.37, 67.33, 50.95, 41.85, 39.04, 28.56, 28.53, 28.47, 28.43, 28.33, 28.25, 25.94, 25.11.

Workup

  1. temperaturecooled in an ice bath
  2. additionAfter the completion of the addition
  3. stirringstirred for 20 hours
  4. washThe solution was washed with water (4×80 mL)
  5. customDrying
  6. concentration(MgSO4) and concentration

Sources & evidence

ORD record
ord-8561a19e2af94ebf92964ff21961eb15
Source dataset
uspto-grants-2000_04
Patent number
US06045821

Reaction notes

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