Propionic Acid → HCID 135853039, compound

HRID 597210Notes

Reaction equation

HRID 597210 reaction equation
[N:1]([O-])=O.[Na+].S(=O)(=O)(O)O.[CH3:10][S:11]([C:14]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:15]=1[NH2:16])(=[O:13])=[O:12].C(O)(=O)CC.[C:29]([NH:33][S:34]([C:37]1[CH:46]=[CH:45][C:44]2[C:39](=[CH:40][CH:41]=[CH:42][C:43]=2[NH:47][S:48]([C:51]2[CH:56]=[CH:55][CH:54]=[C:53]([S:57]([F:60])(=[O:59])=[O:58])[CH:52]=2)(=[O:50])=[O:49])[C:38]=1[OH:61])(=[O:36])=[O:35])([CH3:32])([CH3:31])[CH3:30]>N1C=CC=CC=1.C(O)(=O)C>[C:29]([NH:33][S:34]([C:37]1[CH:46]=[C:45]([N:1]=[N:16][C:15]2[CH:17]=[CH:18][C:19]([N+:21]([O-:23])=[O:22])=[CH:20][C:14]=2[S:11]([CH3:10])(=[O:13])=[O:12])[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][C:43]=2[NH:47][S:48]([C:51]2[CH:56]=[CH:55][CH:54]=[C:53]([S:57]([F:60])(=[O:59])=[O:58])[CH:52]=2)(=[O:49])=[O:50])[C:38]=1[OH:61])(=[O:36])=[O:35])([CH3:32])([CH3:30])[CH3:31]

Participants

8

Reactant 5

HCID 1032Propionic AcidHCID 1118Sulfuric AcidHCID 667852-Mesyl-4-nitroanilineHCID 21446735HCID 21446735, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 135853039HCID 135853039, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1049PyridineSolvent

Conditions

Temperature
25 °C

Procedure

The 2-t-butylsulfamoyl-5-(3-fluorosulfonylbenzenesulfonamido)-4-(2-methylsulfonyl-4-nitrophenylazo)-1-naphthol was prepared by diazo coupling. 7.6 G. (0.11 mol) of sodium nitrite was added to 66 ml. of sulfuric acid at 5° C. and warmed to 70° C. to effect solution. After cooling to 25° C., 23.8 g. (0.11 mol) of 2-methanesulfonyl-4-nitroaniline was added, and the mixture stirred for 2 hours. The diazonium salt mixture was poured into 250 ml. of 1:5 acid (1 part propionic acid to 5 parts acetic acid) at 5° C. A solution of the coupler was prepared by dissolving 51.6 g. (0.1 mol) of 2-t-butylsulfamoyl-5-(3-fluorosulfonylbenzenesulfonamido)-1-naphthol in 66 ml. of pyridine, cooling to 10° C., and adding 520 ml. of the 1:5 acid at 30° C. The diazonium mixture was added to the coupler solution and stirred for one hour at 7° C., the solid collected on a filter funnel and then slurried twice in 500 ml. of 1% hydrochloric acid. The slurry was filtered and the solid dried in a desiccator at 60° C. to yield 25.8 g. of dye. The filtrates from the reaction mixture were diluted to 8000 ml. with water to precipitate additional dye, which was collected on a filter funnel and dried in a desiccator to yield an additional 40 g. (88% total).

Workup

  1. customat 5° C
  2. customA solution of the coupler was prepared
  3. dissolutionby dissolving 51.6 g
  4. additionadding 520 ml
  5. customat 30° C
  6. stirringstirred for one hour at 7° C.
  7. customthe solid collected on a filter funnel
  8. filtrationThe slurry was filtered
  9. customthe solid dried in a desiccator at 60° C.
  10. customto yield 25.8 g
  11. additionThe filtrates from the reaction mixture were diluted to 8000 ml
  12. customwith water to precipitate additional dye, which
  13. customwas collected on a filter funnel
  14. customdried in a desiccator
  15. customto yield an additional 40 g

Sources & evidence

ORD record
ord-6bf07563258b41c6bfb36890fd4f33bc
Source dataset
uspto-grants-1977_03
Patent number
US04013635

Reaction notes

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