Chloroform → HCID 59381658, compound

HRID 2354550Notes

Reaction equation

HRID 2354550 reaction equation
O=P(Cl)(Cl)Cl.CN(C=O)C.[CH3:11][CH:12]1[CH2:18][CH2:17][N:16]2[C:19](=[O:31])[C:20]3[C:25]4[CH2:26][CH2:27][CH2:28][C:29](=[O:30])[C:24]=4[S:23][C:21]=3[N:22]=[C:15]2[CH2:14][CH2:13]1.[CH:32](Cl)(Cl)[Cl:33]>>[Cl:33][C:32]1[C:24]2[S:23][C:21]3[N:22]=[C:15]4[CH2:14][CH2:13][CH:12]([CH3:11])[CH2:18][CH2:17][N:16]4[C:19](=[O:31])[C:20]=3[C:25]=2[CH2:26][CH2:27][C:28]=1[CH:29]=[O:30]

Participants

5

Reactant 4

HCID 6212Chloroform2×HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 59381662HCID 59381662, compound

Product 1

HCID 59381658HCID 59381658, compound

Conditions

Temperature
50 °C

Procedure

POCl3 (2.91 mmol) was added dropwise into DMF (3.02 mmol) in CHCl3 (2 ml) at 0° C. After 30 minutes compound 17 (0.36 mmol) in CHCl3 (6 ml) was added slowly dropwise. The reaction mixture was allowed to reach room temperature and stirred overnight after which the reaction mixture was heated to 50° C. for 12 hours. The reaction mixture was cooled to room temperature and quenched with saturated NaOAc, extracted with CH2Cl2, washed with brine and water, and dried over Na2SO4. After filtration the solvent was evaporated. The product was purified by flash chromatography using CH2Cl2-EtOAc 9:1 as an eluent.

Workup

  1. customto reach room temperature
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customquenched with saturated NaOAc
  4. extractionextracted with CH2Cl2
  5. washwashed with brine and water
  6. dry with materialdried over Na2SO4
  7. filtrationAfter filtration the solvent
  8. customwas evaporated
  9. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-6a08e6886cd04873b1269fbab8340e09
Source dataset
uspto-grants-2010_07
Patent number
US07754709B2

Reaction notes

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