Sulfuryl chloride → Benzenesulfonyl fluoride, 3-[[[6-chloro-5-hydroxy-8-[[2-(methylsulfonyl)-4-nitrophenyl]azo]-1-naphthalenyl]amino]sulfonyl]-

HRID 597211Notes

Reaction equation

HRID 597211 reaction equation
[F:1][S:2]([C:5]1[CH:6]=[C:7]([S:11]([NH:14][C:15]2[CH:24]=[CH:23][CH:22]=[C:21]3[C:16]=2[C:17]([N:26]=[N:27][C:28]2[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][C:29]=2[S:37]([CH3:40])(=[O:39])=[O:38])=[CH:18][CH:19]=[C:20]3[OH:25])(=[O:13])=[O:12])[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].S(Cl)([Cl:44])(=O)=O>>[Cl:44][C:19]1[CH:18]=[C:17]([N:26]=[N:27][C:28]2[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][C:29]=2[S:37]([CH3:40])(=[O:38])=[O:39])[C:16]2[C:21](=[CH:22][CH:23]=[CH:24][C:15]=2[NH:14][S:11]([C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([S:2]([F:1])(=[O:3])=[O:4])[CH:6]=2)(=[O:13])=[O:12])[C:20]=1[OH:25]

Participants

3

Reactant 2

HCID 24648Sulfuryl chlorideHCID 135616739Benzenesulfonyl fluoride, 3-[[[5-hydroxy-8-[[2-(methylsulfonyl)-4-nitrophenyl]azo]-1-naphthalenyl]amino]sulfonyl]-

Product 1

HCID 135666443Benzenesulfonyl fluoride, 3-[[[6-chloro-5-hydroxy-8-[[2-(methylsulfonyl)-4-nitrophenyl]azo]-1-naphthalenyl]amino]sulfonyl]-

Procedure

5-(m-Fluorosulfonylbenzenesulfonamido)-4-(2-methylsulfonyl-4-nitrophenylazo)-1-naphthol (52 g.) (Compound A of Example 13 of U.S. Pat. No. 3,929,760, issued Dec. 30, 1975) is chlorinated by stirring with sulfuryl chloride (200 ml.) for 21 hours at 30°-31° C. The slurry is cooled to 15° and filtered. The resulting solid is then purified by stirring successively with 800 ml. ice water, 100 ml. methanol, 200 ml. acetone (40° C.), and 300 ml. acetone (40°), filtering the resulting slurry each time (acetone precooled to 30°) and washing the solid with the same kind of solvent. The yield is 40.3 g.

Workup

  1. temperatureThe slurry is cooled to 15°
  2. filtrationfiltered
  3. customThe resulting solid is then purified
  4. customacetone (40° C.), and 300 ml
  5. filtrationacetone (40°), filtering the resulting slurry each time (acetone precooled to 30°)
  6. washwashing the solid with the same kind of solvent

Sources & evidence

ORD record
ord-f2997f8f57354aa1b3b280bf96d0e970
Source dataset
uspto-grants-1977_03
Patent number
US04013635

Reaction notes

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