Dimethylformamide → HCID 13393802, compound

HRID 2107728Notes

Reaction equation

HRID 2107728 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([S:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:9][C:10](O)=O.P(Cl)(Cl)([Cl:22])=O.CN(C)[CH:27]=[O:28]>>[Cl:22][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[S:13][CH:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[C:9]=1[CH:27]=[O:28]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 54386794HCID 54386794, compound

Product 1

HCID 13393802HCID 13393802, compound

Procedure

As in example 18, but using 5.4 g 3-(2-fluorophenyl)-3-phenylmercapto-propionic acid, 40 ml dimethylformamide and 15 ml phosphorous oxychloride. After hydrolysis a precipitate forms which is filtered, washed with water and dried over phosphorous pentoxide. The residual solid is recrystallized in hexane and pure yellow crystalline 4-chloro-2'-fluoro-3-formyl-thioflav-3-ene is obtained; m.p. 119°-120° C.

Workup

  1. customAfter hydrolysis a precipitate forms which
  2. filtrationis filtered
  3. washwashed with water
  4. dry with materialdried over phosphorous pentoxide
  5. customThe residual solid is recrystallized in hexane

Sources & evidence

ORD record
ord-a8c0f127143142b19d661fc7863e80e2
Source dataset
uspto-grants-1990_06
Patent number
US04935441

Reaction notes

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