Ethanol → HCID 23471640, compound

HRID 128082Notes

Reaction equation

HRID 128082 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.Br.CS[C:17](=[NH:19])[NH2:18].[CH2:20](O)[CH3:21]>>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([C:17]3[N:19]=[C:21]4[CH:20]=[CH:4][CH:3]=[CH:2][CH:7]=[C:6]4[N:18]=3)[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 13551-(3-Chlorophenyl)piperazineHCID 706061068-58-2

Product 1

HCID 23471640HCID 23471640, compound

Procedure

A mixture of 1-(3-chlorophenyl)piperazine (13 g, described in Example 11) and methylthiomethanimidamide hydrobromide (12.2 g) in ethanol (50 ml) was refluxed for 14 hr and evaporated. To the residue, 1N sodium ethoxide in ethanol (66 ml) and 2-methoxy-2,4,6-cycloheptatrien-1-one(9 g) were added. The mixture was refluxed for 2 hr and evaporated. The residue was chromatographed through a column of silica gel using ethyl acetate and the eluates were evaporated. The residue was crystallized from ethyl acetate to obtain the title compound (5.9 g): mp 217°-219° C; ir(mull)1615, 1590, 1575 and 1530 cm-1 ; uv max (MeOH) 289(ε9.870), 261(ε43,230) and 240 nm(ε29,040); nmr(CDCl3) δ 3.33(4H,t), 4.18(4H,t) and 7.5(9H,m) and Anal. Calcd for C18H17N4Cl: C, 66.56% H, 5.27% N, 17.25% and Found: C, 66.11% H, 5.10% N, 16.99%.

Workup

  1. temperaturewas refluxed for 14 hr
  2. customevaporated
  3. additionTo the residue, 1N sodium ethoxide in ethanol (66 ml) and 2-methoxy-2,4,6-cycloheptatrien-1-one(9 g) were added
  4. temperatureThe mixture was refluxed for 2 hr
  5. customevaporated
  6. customThe residue was chromatographed through a column of silica gel
  7. customthe eluates were evaporated
  8. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-53e4c0b7cb434cb7bd62af64f57c1bcc
Source dataset
uspto-grants-1981_03
Patent number
US04258188

Reaction notes

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