Water → HCID 19348199, compound

HRID 1637290Notes

Reaction equation

HRID 1637290 reaction equation
O[CH:2]1[C:12]2[C:13]3[C:5](=[C:6]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[NH:7][C:8]=3[CH:9]=[CH:10][CH:11]=2)[CH2:4][CH2:3]1.S(Cl)(Cl)=O.[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.O>C(Cl)Cl>[O:27]1[CH2:28][CH2:29][N:24]([CH:2]2[C:12]3[C:13]4[C:5](=[C:6]([C:14]5[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=5)[NH:7][C:8]=4[CH:9]=[CH:10][CH:11]=3)[CH2:4][CH2:3]2)[CH2:25][CH2:26]1

Participants

6

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 24386Thionyl ChlorideHCID 19348302HCID 19348302, compound

Product 1

HCID 19348199HCID 19348199, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A portion (0.47 g) of the compound obtained in Example 256 was suspended in anhydrous methylene chloride (15 ml) and to the suspension was added dropwise a solution of thionyl chloride (0.15 ml) in anhydrous methylene chloride (5 ml) under cooling with ice. After stirring for 30 minutes, a solution (10 ml) of morpholine (1.65 ml) in anhydrous methylene chloride was added dropwise and the mixture was stirred for 3 hours. Water was added to the reaction mixture, followed by extraction with methylene chloride. The organic layer was washed with water and saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was washed with diethyl ether and methanol to yield 0.38 g (63%) of the titled compound as pale yellow crystals.

Workup

  1. temperatureunder cooling with ice
  2. stirringthe mixture was stirred for 3 hours
  3. extractionfollowed by extraction with methylene chloride
  4. washThe organic layer was washed with water and saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. washThe residue was washed with diethyl ether and methanol

Sources & evidence

ORD record
ord-13f9ba3f7f3c49489bf66c046d38d3c2
Source dataset
uspto-grants-2000_03
Patent number
US06040331

Reaction notes

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