Ammonia → HCID 20546728, compound

HRID 2059201Notes

Reaction equation

HRID 2059201 reaction equation
[ClH:1].[CH3:2][C:3]1[S:19][C:6]2[CH2:7][N:8]([CH3:18])[CH2:9][CH:10]([C:11]3[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=3)[C:5]=2[CH:4]=1.[Br-:20].[Al+3].[Br-].[Br-].BrBr.N>C(O)(=O)C>[ClH:1].[CH3:2][C:3]1[S:19][C:6]2[CH2:7][N:8]([CH3:18])[CH2:9][CH:10]([C:11]3[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=3)[C:5]=2[C:4]=1[Br:20]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 24408BromineHCID 166749BromhydrolHCID 20546707HCID 20546707, compound

Product 1

HCID 20546728HCID 20546728, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
15 °C

Procedure

3 gm (0.008 mol) of 2,6-dimethyl-4-(p-bromophenyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine hydrochloride and 8 gm of aluminum bromide were dissolved in 100 ml of glacial acetic acid. The solution was cooled to 15° C., 1.4 gm of bromine were slowly added dropwise and the mixture was stirred several hours until the reaction had gone to completion. Then, the mixture was decomposed with ice water, made alkaline with ammonia, extracted with ethyl acetate and evaporated. The residue was chromatographed on silicagel with methylene chloride/methanol (95:5). Upon addition of ethereal hydrochloric acid, 2.25 gm (61% of theory) of the title compound, m.p. 261°-262° C., were obtained.

Workup

  1. extractionextracted with ethyl acetate
  2. customevaporated
  3. customThe residue was chromatographed on silicagel with methylene chloride/methanol (95:5)
  4. additionUpon addition of ethereal hydrochloric acid, 2.25 gm (61% of theory) of the title compound, m.p. 261°-262° C.
  5. customwere obtained

Sources & evidence

ORD record
ord-e2004524b80f45d499ef14ccfb649ff8
Source dataset
uspto-grants-1982_03
Patent number
US04322423

Reaction notes

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