Dichloromethane → HCID 178470106, compound

HRID 1382744Notes

Reaction equation

HRID 1382744 reaction equation
C(Cl)Cl.[OH:4][C:5]1[C:14]2[C:9](=[C:10]([F:17])[C:11]([F:16])=[C:12]([F:15])[CH:13]=2)[N:8]=[C:7]([SH:18])[C:6]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20].C(N(CC)CC)C.[C:31]([O:34][CH2:35][C:36]([CH2:38]Cl)=[O:37])(=[O:33])[CH3:32]>C(Cl)(Cl)Cl>[C:31]([O:34][CH2:35][C:36](=[O:37])[CH2:38][S:18][C:7]1[C:6]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:5]([OH:4])[C:14]2[C:9](=[C:10]([F:17])[C:11]([F:16])=[C:12]([F:15])[CH:13]=2)[N:8]=1)(=[O:33])[CH3:32]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 384132-Propanone, 1-(acetyloxy)-3-chloro-HCID 178470134HCID 178470134, compound

Product 1

HCID 178470106HCID 178470106, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To methylene chloride (500 ml) were added ethyl 4-hydroxy-2-mercapto-6,7,8-trifluoroquinoline-3-carboxylate (33 g), triethylamine (22 g) and 1-acetoxy-3-chloroacetone (16.4 g) and the mixture was stirred at room temperature for 15 minutes. Chloroform (700 ml) was added to the reaction solution and washed with 0.1N hydrochloric acid, water and a NaCl solution in this order, dried over anhydrous magnesium sulfate and evaporated to dryness under reduced pressure. The residue was recrystallized from ethyl acetate to give the title compound (37.2 g) as colorless crystals, m.p. 175°-180° C.

Workup

  1. washwashed with 0.1N hydrochloric acid, water
  2. dry with materiala NaCl solution in this order, dried over anhydrous magnesium sulfate
  3. customevaporated to dryness under reduced pressure
  4. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-06f6941a76a14c0bb2d2d51f9d101ac5
Source dataset
uspto-grants-1989_02
Patent number
US04808584

Reaction notes

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