Water → HCID 19972563, compound

HRID 1653799Notes

Reaction equation

HRID 1653799 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-5ceddf2a77d24c178e972c1560178d99
Source dataset
uspto-grants-1995_04
Patent number
US05403842

Reaction notes

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