Water → HCID 22504861, compound

HRID 1296056Notes

Reaction equation

HRID 1296056 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([CH2:17]O)=[CH:13][C:11]=3[N:12]=2)[CH:5]=[CH:6][CH:7]=1.O=S(Cl)[Cl:21].C(=O)(O)[O-].[Na+].O>ClCCl>[Cl:21][CH2:17][C:14]1[CH:15]=[CH:16][C:10]2[O:9][C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)=[N:12][C:11]=2[CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 22504740HCID 22504740, compound

Product 1

HCID 22504861HCID 22504861, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 69B was suspended in 100 ml dichloromethane. SOCl2 was added and allowed to stir for 2 h. 20 ml Saturated sodium bicarbonate was added followed by 20 ml water and stirred for 5 minutes. The dichloromethane layer was seperated and dried over anhydrous sodium sulfate. The dichloromethane solution was filtered through silica and eluted with dichloromethane until clear. Concentration of the filtrate gave a pink solid. MS m/z 262 (M+1).

Workup

  1. stirringstirred for 5 minutes
  2. customThe dichloromethane layer was seperated
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe dichloromethane solution was filtered through silica
  5. washeluted with dichloromethane until clear
  6. customConcentration of the filtrate gave a pink solid

Sources & evidence

ORD record
ord-316ad068f5e24d938e28ba117fcd8dab
Source dataset
uspto-grants-2007_07
Patent number
US07244763B2

Reaction notes

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