Hydrochloric Acid → Calcium 3-methylsulfonyl-4-(2-acetylamino-5-chloro-4-hydroxyphenylazo)phenylsulfonate

HRID 1252024Notes

Reaction equation

HRID 1252024 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([Cl:12])=[C:9]([OH:11])[CH:10]=1)(=[O:3])[CH3:2].[OH-].[Na+].[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([O-:25])(=[O:24])=[O:23])=[CH:18][C:17]=1[S:26]([CH3:29])(=[O:28])=[O:27].[Ca+2:30].[NH2:31][C:32]1[CH:37]=[CH:36][C:35]([S:38]([O-:41])(=[O:40])=[O:39])=[CH:34][C:33]=1[S:42]([CH3:45])(=[O:44])=[O:43].[N:46](OS(=O)(=O)O)=O.Cl.[Cl-].[Ca+2].[Cl-]>C(#N)C>[CH3:29][S:26]([C:17]1[CH:18]=[C:19]([S:22]([O-:25])(=[O:23])=[O:24])[CH:20]=[CH:21][C:16]=1[N:15]=[N:31][C:6]1[CH:7]=[C:8]([Cl:12])[C:9]([OH:11])=[CH:10][C:5]=1[NH:4][C:1](=[O:3])[CH3:2])(=[O:28])=[O:27].[Ca+2:30].[CH3:45][S:42]([C:33]1[CH:34]=[C:35]([S:38]([O-:41])(=[O:39])=[O:40])[CH:36]=[CH:37][C:32]=1[N:31]=[N:46][C:6]1[CH:7]=[C:8]([Cl:12])[C:9]([OH:11])=[CH:10][C:5]=1[NH:4][C:1](=[O:3])[CH3:2])(=[O:44])=[O:43]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 82157Nitrosylsulfuric acidHCID 5284359Calcium ChlorideHCID 14122483N-(4-Chloro-3-hydroxyphenyl)acetamideHCID 14122484Calcium 4-amino-3-methylsulfonylphenylsulfonate

Product 1

HCID 136342787Calcium 3-methylsulfonyl-4-(2-acetylamino-5-chloro-4-hydroxyphenylazo)phenylsulfonate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution containing 18.6 g (0.1 mole) of 5-acetylamino-2-chlorophenol, 100 ml of 0.2 N sodium hydroxide, and 50 ml of acetonitrile was maintained at a temperature of 5° C. or less with stirring. Separately, 32.4 g (0.12 mole) of calcium 4-amino-3-methylsulfonylphenylsulfonate was diazotized with nitrosylsulfuric acid in the routine manner and the resulting diazo solution was added in portions to the above solution. After completion of the addition, 0.2N sodium hydroxide was added dropwise with ice-cooling unil the pH of the mixture became 4 to 5. After 30 minutes, the reaction mixture was adjusted to a pH value not exceeding 2 with 36% hydrochloric acid and 100 g of calcium chloride was added for salting-out. The crystalline precipitate was collected by filtration, washed with 50 ml of methanol and dried.

Workup

  1. temperaturewas maintained at a temperature of 5° C. or less
  2. additionwas added dropwise with ice-
  3. temperaturecooling
  4. additionwas added for salting-out
  5. filtrationThe crystalline precipitate was collected by filtration
  6. washwashed with 50 ml of methanol
  7. customdried

Sources & evidence

ORD record
ord-98d5cca047ef4475bca1a29fa64ad33f
Source dataset
uspto-grants-1988_05
Patent number
US04741997

Reaction notes

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