Water → HCID 67040418, compound

HRID 605249Notes

Reaction equation

HRID 605249 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:26])[C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([N:23]([CH3:25])[CH3:24])[CH:18]=3)=[CH:11][C:10]=2[N+:27]([O-:29])=[O:28])=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[C:37]([O:39][CH2:40][C:41](Cl)([Cl:43])[Cl:42])=[O:38].O>ClCCl>[Cl:42][CH:41]([Cl:43])[CH2:40][O:39][C:37](=[O:38])[NH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:26])[C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([N:23]([CH3:25])[CH3:24])[CH:18]=3)=[CH:11][C:10]=2[N+:27]([O-:29])=[O:28])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 67040855HCID 67040855, compound

Product 1

HCID 67040418HCID 67040418, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 239c (2.8 g, 6.8 mmol) in dichloromethane (40 mL) was added pyridine (1.1 g, 13.7 mmol) and 2,2,2-trichloroethyl chloroformate (1.7 g, 2.8 mmol). The mixture was stirred at room temperature for 72 h. The reaction was poured into water. The aqueous phase was extracted with ethyl acetate (2×). The combined organic phases were washed with water, brine, and dried over sodium sulfate, filtered and concentrated under vacuum giving the title compound. The residue was purified by silica gel chromatography eluting with hexane/ethyl acetate/methanol (80:15:5) to give the desired product (2.0 g, 53%).

Workup

  1. extractionThe aqueous phase was extracted with ethyl acetate (2×)
  2. washThe combined organic phases were washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-330233d200e94e51bc37989beafd6247
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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