Diisopropylethylamine → HCID 54141264, compound

HRID 1769099Notes

Reaction equation

HRID 1769099 reaction equation
Br.[Br:2][C:3]1[S:4][C:5]([Br:11])=[C:6]2[CH2:10][NH:9][CH2:8][C:7]=12.[C:12]1([C:18]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:19]2[CH:23]=[C:22]([CH2:24]Cl)[N:21]=[CH:20]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[Br:2][C:3]1[S:4][C:5]([Br:11])=[C:6]2[CH2:10][N:9]([CH2:24][C:22]3[N:21]=[CH:20][N:19]([C:18]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH:23]=3)[CH2:8][C:7]=12

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27631764-(Chloromethyl)-1-trityl-1H-imidazoleHCID 18947067HCID 18947067, compound

Product 1

HCID 54141264HCID 54141264, compoundYield 32.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.5 g (4.1 mmol) of 1,3-dibromo-5,6-dihydro-4H-thieno[3,4-c]pyrrole hydrobromide, 2.12 g (5.9 mmol) of 1-triphenylmethyl-4-chloromethylimidazole, 30 ml of dimethylformamide and 1.54 ml (9 mmol) of N,N-diisopropylethylamine are introduced into a 50 ml round-bottomed flask. The reaction mixture is subjected to ultrasound for 2 hours and is then poured onto ice. The precipitate obtained is filtered, washed with water, taken up in 50 ml of ethyl acetate, dried over sodium sulphate, filtered and evaporated to dryness. The residue is purified by chromatography on silica gel using the 1/1 ethyl acetate/hexane eluent mixture. 0.8 g of a white solid is obtained. Yield 32%.

Workup

  1. additionis then poured onto ice
  2. customThe precipitate obtained
  3. filtrationis filtered
  4. washwashed with water
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe residue is purified by chromatography on silica gel using the 1/1 ethyl acetate/hexane eluent mixture

Sources & evidence

ORD record
ord-7f026182d87d48428b1f06dd1b64fa21
Source dataset
uspto-grants-1995_01
Patent number
US05380742

Reaction notes

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