2-Thiopheneacetyl chloride → HCID 10238584, compound

HRID 1071395Notes

Reaction equation

HRID 1071395 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH2:18])[CH2:8][CH2:7]1.[S:23]1[CH:27]=[CH:26][CH:25]=[C:24]1[CH2:28][C:29](Cl)=[O:30]>C(N(CC)CC)C.ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:5][N:6]1[CH2:7][CH2:8][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH:18][C:29](=[O:30])[CH2:28][C:24]2[S:23][CH:27]=[CH:26][CH:25]=2)[CH2:10][CH2:11]1

Participants

5

Reactant 2

HCID 1623622-Thiopheneacetyl chlorideHCID 11325154HCID 11325154, compound

Product 1

HCID 10238584HCID 10238584, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

2-[4-(3,4-dichlorobenzyl)-piperazin-1-yl]-phenylamine (45 mg) was dissolved in a solution of triethylamine in dichloromethane (3 mL, 0.29 M in triethylamine). This solution was added to a test tube containing 2-thiopheneacetyl chloride (50 mg). After standing at ambient temperature for several days, the reaction was directly passed through a small pad of silica and eluted with 10% ethyl acetate in hexanes, then with 50% ethyl acetate in hexanes. Solvent removal left 48.6 mg of the product: MS m/z 459 (M)+.

Workup

  1. additionThis solution was added to a test tube
  2. waitAfter standing at ambient temperature for several days
  3. washeluted with 10% ethyl acetate in hexanes
  4. customSolvent removal
  5. waitleft 48.6 mg of the product

Sources & evidence

ORD record
ord-99f5f080377e46f49f04d8aa80a5d0d3
Source dataset
uspto-grants-2005_06
Patent number
US06906073B2

Reaction notes

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