Dimethylformamide → HCID 13393801, compound

HRID 2107727Notes

Reaction equation

HRID 2107727 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([S:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][C:10](O)=O)=[CH:4][CH:3]=1.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:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[C:9]=1[CH:27]=[O:28]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 10423574HCID 10423574, compound

Product 1

HCID 13393801HCID 13393801, compound

Procedure

As in example 18, but using 4.6 g 3-(4-fluorophenyl)-3-phenylmercapto-propionic acid, 40 ml dimethylformamide and 15 ml phosphorous oxychloride. After hydrolysis and work-up a residual oil is obtained which is purified by preparative HPLC. The oily fractions are crystallized in hexane and pure 4-chloro-4'-fluoro-3-formyl-thio-flav-3-ene is obtained as yellow crystals; m.p. 67°-69° C.

Workup

  1. customAfter hydrolysis
  2. customis obtained which
  3. customis purified by preparative HPLC
  4. customThe oily fractions are crystallized in hexane

Sources & evidence

ORD record
ord-45a92c82c9c548ddad03a02c58941dd4
Source dataset
uspto-grants-1990_06
Patent number
US04935441

Reaction notes

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