N,N,N',N'-Tetramethylethylenediamine → HCID 53867368, compound

HRID 1493735Notes

Reaction equation

HRID 1493735 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].ClC1C=CC=CC=1C[N:10]1[CH:14]=[N:13][CH:12]=[N:11]1.CN(C)[CH2:21][CH2:22]N(C)C.[CH:27]12[CH2:36][CH:31]3[CH2:32][CH:33]([CH2:35][CH:29]([CH2:30]3)[C:28]1=[O:37])[CH2:34]2.O.[CH2:39]([Cl:41])Cl>CCCCCC.O1CCCC1>[Cl:41][C:39]1[CH:4]=[CH:3][CH:2]=[CH:1][C:21]=1[CH2:22][C:14]1[N:10]([C:27]23[CH2:36][CH:31]4[CH2:32][CH:33]([CH2:35][CH:29]([CH2:30]4)[CH:28]2[OH:37])[CH2:34]3)[N:11]=[CH:12][N:13]=1

Participants

8

Reactant 5

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 64151AdamantanoneHCID 19902100HCID 19902100, compoundHCID 21908982Water methylene chlorideHCID 178418339Butyllithium

Product 1

HCID 53867368HCID 53867368, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

66 ml (100 mmol) of n-butyllithium in hexane were added dropwise, at -78° C., to a solution of 9,7 g (50 mmol) of 1-(2-chlorobenzyl)-1,2,4-triazole and 6 g (50 mmol) of N,N,N',N'-tetramethylethylenediamine in 100 ml of tetrahydrofuran, stirring was carried out for a further half an hour at this temperature and 7.5 g (50 mmol) of adamantanone in tetrahydrofuran were then added so that -70° C. was not exceeded. The reaction mixture was kept at -78° C. for a further 2 hours and then allowed to warm up to room temperature. After working up with water/methylene chloride, 17.4 g of crude product were obtained, and this product gave 10.0 g of pure triazole derivative of melting point 178° C. after recrystallization from ethyl acetate.

Workup

  1. additionwere then added so that -70° C.
  2. custom17.4 g of crude product were obtained

Sources & evidence

ORD record
ord-7193549bd25c4ffcb14e566c50530a5f
Source dataset
uspto-grants-1991_06
Patent number
US05023357

Reaction notes

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