Water → HCID 19972563, compound

HRID 2400173Notes

Reaction equation

HRID 2400173 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 chloroacetyl chloride in 32 ml of 1,2-dichloroethane was added dropwise with stirring at -5° C. to a mixture of 10 g of Intermediate XIV and 5.5 ml of triethylamine in 80 ml of 1,2-dichloroethane. The reaction mixture was stirred at ambient temperature for 1 hour, then 150 ml of water was added. The phases were separated and the aqueous phase was extracted with 1,2-dichloroethane. The extracts were combined with the organic phase and washed with a cold saturated sodium bicarbonate solution and water, then dried on anhydrous sodium sulphate. Solvent was removed in vacuo and the resultant residue was crystallized from ethanol to give 10.7 g of the title compound, melting point 152°-155° C.

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with 1,2-dichloroethane
  3. washwashed with a cold saturated sodium bicarbonate solution and water
  4. dry with materialdried on anhydrous sodium sulphate
  5. customSolvent was removed in vacuo
  6. customthe resultant residue was crystallized from ethanol

Sources & evidence

ORD record
ord-b00f8bb2ae7b47059af3150eb9131caa
Source dataset
uspto-grants-1995_09
Patent number
US05453518

Reaction notes

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