Chloroacetyl chloride → HCID 14027767, compound

HRID 464390Notes

Reaction equation

HRID 464390 reaction equation
[NH2:1][CH:2]1[C:12]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][O:5][C:4]2[CH:13]=[CH:14][CH:15]=[CH:16][C:3]1=2.C(N(CC)CC)C.[Cl:24][CH2:25][C:26](Cl)=[O:27]>ClCCl>[Cl:24][CH2:25][C:26]([NH:1][CH:2]1[C:12]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][O:5][C:4]2[CH:13]=[CH:14][CH:15]=[CH:16][C:3]1=2)=[O:27]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 13518620HCID 13518620, compound

Product 1

HCID 14027767HCID 14027767, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In this example, 1.9 g of 5-amino-5,11-dihydro[1]benzoxepino[3,4-b]pyridine prepared in a similar manner to that in Example 24 and 0.9 g of triethylamine were dissolved in 30 ml of dichloromethane. A solution of 1.0 g of chloroacetyl chloride in 5 ml of dichloromethane was added dropwise thereto under ice cooling. The mixture was stirred under ice cooling for 2 hours, and concentrated under reduced pressure to distill away about two thirds of the dichloromethane. Then, 40 ml of diisopropyl ether and 10 ml of water were added thereto, and the mixture was stirred and filtered. Drying the residue gave 2.3 g of 5-(chloroacetyl)amino-5,11-dihydro[1]benzoxepino[3,4-b]pyridine as crude crystals.

Workup

  1. concentrationconcentrated under reduced pressure
  2. distillationto distill away about two thirds of the dichloromethane
  3. additionThen, 40 ml of diisopropyl ether and 10 ml of water were added
  4. stirringthe mixture was stirred
  5. filtrationfiltered
  6. customDrying the residue

Sources & evidence

ORD record
ord-e64de7b2d1224e6db1957a9dcbdbdd94
Source dataset
uspto-grants-1985_10
Patent number
US04547496

Reaction notes

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