Water → HCID 19972563, compound

HRID 1452295Notes

Reaction equation

HRID 1452295 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[NH2:6][CH2:7][C:8]1[C:17]2[O:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:14]([CH3:24])[C:13](=[O:25])[C:12]=2[CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C.O>ClCCCl>[Cl:1][CH2:2][C:3]([NH:6][CH2:7][C:8]1[C:17]2[O:16][C:15]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[C:14]([CH3:24])[C:13](=[O:25])[C:12]=2[CH:11]=[CH:10][CH:9]=1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 19972800HCID 19972800, compound

Product 1

HCID 19972563HCID 19972563, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

A solution of 3.2 ml of chloracetyl chloride in 32 ml of 1,2-dichloroethane was added dropwise, under stirring at -5° C., to a mixture of 10 g of Intermediate XXIV and 5.5 ml of triethylamine in 80 ml of 1,2-dichloroethane. The reaction mixture was stirred at ambient temperature for 1 hour and then 150 ml of water was added. The phases were separated; the aqueous phase was extracted with 1,2-dichloroethane and the extracts were added to the organic phase which was then washed with a cold saturated solution of sodium bicarbonate, washed with water, dried on anhydrous sodium sulfate and evaporated to dryness in vacuo. The residue was crystallized from ethanol to give 10.7 g of the title compound, m.p. 152°-155° C.

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with 1,2-dichloroethane
  3. additionthe extracts were added to the organic phase which
  4. washwas then washed with a cold saturated solution of sodium bicarbonate
  5. washwashed with water
  6. dry with materialdried on anhydrous sodium sulfate
  7. customevaporated to dryness in vacuo
  8. customThe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-f94d673d0df448b790d3ddd4d8ad6b59
Source dataset
uspto-grants-1997_02
Patent number
US05605896

Reaction notes

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