Hydrochloric Acid → 5-((4-((2-Carboxyethyl)carbamoyl)phenyl)diazenyl)-2-hydroxybenzoic acid

HRID 916723

反応式

HRID 916723 の反応式
[NH2:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([NH:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[O:7])=[CH:4][CH:3]=1.CS(O)(=O)=O.[N:21]([O-])=O.[Na+].[C:25]([OH:34])(=[O:33])[C:26]1[C:27](=[CH:29][CH:30]=[CH:31][CH:32]=1)[OH:28].[OH-].[Na+].C(=O)([O-])[O-].[Na+].[Na+].Cl>O>[CH:14]1[C:5]([C:6]([NH:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[O:7])=[CH:4][CH:3]=[C:2]([N:1]=[N:21][C:31]2[CH:30]=[CH:29][C:27]([OH:28])=[C:26]([C:25]([OH:34])=[O:33])[CH:32]=2)[CH:15]=1

参加物

9

反応物 7

HCID 313Hydrochloric AcidHCID 338Salicylic AcidHCID 6395Methanesulfonic AcidHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 719629N-(4-Aminobenzoyl)-beta-alanineHCID 23668193Sodium Nitrite

生成物 1

HCID 545855-((4-((2-Carboxyethyl)carbamoyl)phenyl)diazenyl)-2-hydroxybenzoic acid収率 90%

試薬・触媒・溶媒 1

HCID 962Water溶媒3 回

反応条件

温度
10 °C

実験手順

N-(4-Aminobenzoyl)-β-alanine (100 g) was suspended in water (1300 mL) and methanesulfonic acid (115.4 g) was added to this mixture. The mixture was cooled to 10° C. and a solution of sodium nitrite (34.46 g) in water (200 mL) was added at a rate such that the temperature stayed below 12° C. The mixture was stirred for 30 min and added to an ice-cold solution of salicylic acid (69.65 g), sodium hydroxide (40.35 g) and sodium carbonate (106.9 g) in 1 L water at 7-12° C. After 3 hours at 10° C., the mixture was heated to 60-65° C. and acidified to pH 4.0-4.5 by the addition of hydrochloric acid. After a further 3 hours at 60-65° C., the mixture was cooled to ambient temperature, filtered, washed with water and dried in vacuo to yield Balsalazide. Yield ca. 90%. Balsalazide was transformed into its disodium salt in ca. 85% yield by treatment with aqueous NaOH solution followed by crystallization from n-propanol/methanol.

後処理

  1. customstayed below 12° C
  2. waitAfter 3 hours at 10° C.
  3. temperaturethe mixture was heated to 60-65° C.
  4. waitAfter a further 3 hours at 60-65° C.
  5. temperaturethe mixture was cooled to ambient temperature
  6. filtrationfiltered
  7. washwashed with water
  8. customdried in vacuo

出典と根拠

ORDレコード
ord-01acf431bb1044b4897a34e596b18957
出典データセット
uspto-grants-2007_09
特許番号
US07271253B1

関連ノート

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