Dimethylformamide → alpha-(2-Benzoyloxy-5-chlorosulfonylphenylazo)-beta-benzoyloxycinnamonitrile

HRID 26121Notes

Reaction equation

HRID 26121 reaction equation
[C:1]([O:9][C:10]1[C:11]([N:19]=[N:20][C:21](=[C:24]([O:31][C:32](=[O:39])[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:22]#[N:23])=[CH:12][C:13](=[S:16](=[O:18])=[O:17])[CH2:14][CH:15]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)C=O.S(Cl)([Cl:47])=O>>[C:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([Cl:47])(=[O:18])=[O:17])=[CH:12][C:11]=1[N:19]=[N:20][C:21](=[C:24]([O:31][C:32](=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:22]#[N:23])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 86736451alpha-(2-Benzoyloxy-5-sulfonylphenylazo)-beta-benzoyloxycinnamonitrile

Product 1

HCID 54435792alpha-(2-Benzoyloxy-5-chlorosulfonylphenylazo)-beta-benzoyloxycinnamonitrile

Procedure

To a solution of α-(2-benzoyloxy-5-sulfonylphenylazo)-β-benzoyloxycinnamonitrile (10 g) in 50 ml of thionyl chloride was added 3 ml of dimethylformamide. The reaction mixture was allowed to stir at room temperature for 31/2 hours. The solvent was evaporated to dryness under vacuum at room temperature. The residue was diluted with ethyl ether (50 ml) to form a white precipitate. The product was filtered off and dried to yield 9.4 g, m.p. 153° to 155° C.

Workup

  1. customThe solvent was evaporated to dryness under vacuum at room temperature
  2. additionThe residue was diluted with ethyl ether (50 ml)
  3. customto form a white precipitate
  4. filtrationThe product was filtered off
  5. customdried
  6. customto yield 9.4 g, m.p. 153° to 155° C.

Sources & evidence

ORD record
ord-85126a72ba6a4c5b963c42489c052c48
Source dataset
uspto-grants-1979_04
Patent number
US04148643

Reaction notes

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