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Dimethylformamide → HCID 86752547, compound

HRID 1289779
Notes
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Reaction equation

HRID 1289779 reaction equation
[NH2:1][C:2]1[N:6]=[C:5]([NH2:7])[N:4]([C:8]([NH:10][CH3:11])=[S:9])[N:3]=1.CN(C)[CH:14]=[O:15].[CH2:17](N(CC)CC)C.CC[C:26]([C:28](Cl)=[O:29])=[O:27]>O.C(Cl)(Cl)Cl>[NH2:7][C:5]1[N:4]([C:8]([NH:10][CH3:11])=[S:9])[N:3]=[C:2]([NH:1][C:26]([C:28]([O:15][CH2:14][CH3:17])=[O:29])=[O:27])[N:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 10725863HCID 10725863, compoundHCID 11007880Butanoyl chloride, 2-oxo-

Product 1

HCID 86752547HCID 86752547, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6212ChloroformSolvent

Procedure

The compound (4.00 g) obtained in Example 31, dimethylformamide (80 ml) and triethylamine (3.9 ml) were cooled to 0° C. Ethyloxalyl chloride (2.7 ml) was gradually added dropwise and the mixture was stirred at 0° C.-room temperature for 2.5 hours. After the stirring, chloroform (50 ml) was added and the mixture was stirred at 0° C. for 30 minutes. The reaction mixture was poured into water and extracted with chloroform. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure to give a pale-yellow liquid. This liquid was subjected to silica gel column chromatography (chloroform-methanol) and recrystallization from ethanol to give 1.22 g of white powdery crystals (yield 19%).

Workup

  1. stirringthe mixture was stirred at 0° C. for 30 minutes
  2. extractionextracted with chloroform
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled away under reduced pressure
  6. customto give a pale-yellow liquid
  7. customThis liquid was subjected to silica gel column chromatography (chloroform-methanol) and recrystallization from ethanol

Sources & evidence

ORD record
ord-6954eba5541e4d9db465f6ba146872f2
Source dataset
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05750545

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes