Dimethylformamide → HCID 68129031, compound

HRID 1077048Notes

Reaction equation

HRID 1077048 reaction equation
[CH2:1]1[C:11]2[N:10]3[C:12]4[CH:21]=[CH:20][N:19]=[CH:18][C:13]=4[C:14]4[CH2:15][CH2:16][CH:17]=[C:8]([C:9]=43)[CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3][CH2:2]1.[Cl:22][CH:23]([CH:25]1[CH2:27][CH2:26]1)[CH3:24].C(=O)(O)[O-].[Na+].CN(C)C=O>O>[ClH:22].[CH:25]1([CH:23]([CH:3]2[CH2:4][C:5]3[CH:6]=[CH:7][C:8]4[C:9]5[N:10]([C:12]6[CH:21]=[CH:20][N:19]=[CH:18][C:13]=6[C:14]=5[CH2:15][CH2:16][CH:17]=4)[C:11]=3[CH2:1][CH2:2]2)[CH3:24])[CH2:27][CH2:26]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 12627052(1-chloroethyl)cyclopropaneHCID 67838308HCID 67838308, compound

Product 1

HCID 68129031HCID 68129031, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5.5 g. of the product of Example 1, 2.3 g. of (1-chloroethyl)cyclopropane and 3.0 g. of sodium bicarbonate in 100 ml. of dimethylformamide is heated to 70°, with continued stirring, overnight, and the reaction mixture is then poured into water and extracted with ether. The extract is dried, evaporated to dryness, and the residue is dissolved in benzene and chromatographed. The eluate is then evaporated to dryness, the residue dissolved in absolute alcohol, treated with alcoholic hydrogen chloride, stripped down to dryness, and the glassy residue triturated with acetone to yield white crystals of the title compound, m.p. 249°-252°.

Workup

  1. additionA mixture of 5.5 g
  2. extractionextracted with ether
  3. customThe extract is dried
  4. customevaporated to dryness
  5. dissolutionthe residue is dissolved in benzene
  6. customchromatographed
  7. customThe eluate is then evaporated to dryness
  8. dissolutionthe residue dissolved in absolute alcohol
  9. additiontreated with alcoholic hydrogen chloride
  10. customthe glassy residue triturated with acetone

Sources & evidence

ORD record
ord-0e5a5076366a41d0a24425f37933fbb1
Source dataset
uspto-grants-1976_05
Patent number
US03959300

Reaction notes

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