N,N,N',N'-Tetramethylazodicarboxamide → HCID 21552323, compound

HRID 268143Notes

Reaction equation

HRID 268143 reaction equation
[CH2:1]([N:3]([CH2:9][CH3:10])[CH2:4][CH2:5][CH2:6][Mg]Cl)[CH3:2].[CH2:11]([N:13]([CH2:18][CH3:19])[CH2:14][CH2:15][CH2:16]Cl)[CH3:12].[C:20](C1C=CC2C3C(=CC=C(C#N)C=3)N(C)C=2C=1)#N.[CH:38]1[C:50]2[NH:49][C:48]3[C:43](=[CH:44][C:45]([C:51](N)=[O:52])=[CH:46][CH:47]=3)[C:42]=2[CH:41]=[CH:40][C:39]=1[C:54](N)=[O:55].COS(OC)(=O)=O.[OH-].[Na+].CN(C(N=NC(N(C)C)=O)=O)C.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[Cl-].[NH4+]>O1CCCC1>[CH2:1]([N:3]([CH2:9][CH3:10])[CH2:4][CH2:5][CH2:6][C:54]([C:39]1[CH:40]=[CH:41][C:42]2[C:43]3[C:48](=[CH:47][CH:46]=[C:45]([C:51](=[O:52])[CH2:16][CH2:15][CH2:14][N:13]([CH2:18][CH3:19])[CH2:11][CH3:12])[CH:44]=3)[N:49]([CH3:20])[C:50]=2[CH:38]=1)=[O:55])[CH3:2]

Participants

11

Reactant 9

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 14812Phosphorus oxide (P4O10)HCID 25517Ammonium ChlorideHCID 669183-Chloropropyl(diethyl)amineHCID 21552327HCID 21552327, compoundHCID 21552927HCID 21552927, compoundHCID 178463982HCID 178463982, compound

Product 1

HCID 21552323HCID 21552323, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2.5 equivalents of 3-diethylaminopropylmagnesium chloride and 3-diethylaminopropylchloride in tetrahydrofuran, is added dropwise a solution of 1-equivalent of 2,6-dicyano-N-methylcarbazole, which is prepared by converting 2,6-carbazoledicarboxamide to the corresponding N-methyl derivative by treatment with dimethylsulfate in the presence of sodium hydroxide and subsequently dehydrating the diamide by heating with phosphorous pentoxide, in tetrahydrofuran. When the addition is complete the reaction mixture is gently refluxed for 2 hours, then stirred at room temperature for several hours. The resulting complex is decomposed by treatment with saturated ammonium chloride, and the organic material is extracted with chloroform. The chloroform layer is treated with dilute HCl with warming. The aqueous solution is filtered, made alkaline and extracted with ether. The ether extract is dried over magnesium sulfate and evaporated to dryness to give the desired product.

Workup

  1. customis prepared
  2. additionWhen the addition
  3. temperatureis gently refluxed for 2 hours
  4. extractionthe organic material is extracted with chloroform
  5. additionThe chloroform layer is treated with dilute HCl
  6. temperaturewith warming
  7. filtrationThe aqueous solution is filtered
  8. extractionextracted with ether
  9. extractionThe ether extract
  10. dry with materialis dried over magnesium sulfate
  11. customevaporated to dryness

Sources & evidence

ORD record
ord-50a69b7246e14d46a28de88f7781f5ab
Source dataset
uspto-grants-1976_03
Patent number
US03946021

Reaction notes

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