Aniline → HCID 23345442, compound

HRID 1856482Notes

Reaction equation

HRID 1856482 reaction equation
[Cl:1][C:2]1[S:6][CH:5]=[C:4]([C:7]([NH2:9])=[O:8])[C:3]=1[O:10][CH2:11][CH3:12].C(Cl)Cl.N[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(N(CC)CC)C>[Cl:1][C:2]1[S:6][CH:5]=[C:4]([C:7]([NH:9][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:8])[C:3]=1[O:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 6115AnilineHCID 6344DichloromethaneHCID 23345440HCID 23345440, compound

Product 1

HCID 23345442HCID 23345442, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A 4.50 g. portion of 5-chloro-4-ethoxy-3-thiophenecarbonyl chloride (prepared as in Example 4) was dissolved in 40 ml. of methylene chloride and stirred overnight with 2.8 ml. of triethylamine and 1.86 g. of aniline. The mixture was filtered and the filtrate extracted with 3 N hydrochloric acid. The methylene chloride layer was treated with activated charcoal, dried over anhydrous sodium sulfate and diluted with petroleum ether to give 3.62 g. of the product of the example as a white crystalline solid, m.p. 69° C.

Workup

  1. filtrationThe mixture was filtered
  2. extractionthe filtrate extracted with 3 N hydrochloric acid
  3. additionThe methylene chloride layer was treated with activated charcoal
  4. dry with materialdried over anhydrous sodium sulfate
  5. additiondiluted with petroleum ether
  6. customto give 3.62 g

Sources & evidence

ORD record
ord-06676c09307541e39768189b3047e7d5
Source dataset
uspto-grants-1980_08
Patent number
US04219656

Reaction notes

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