Water → 2-Aminomethyl-4-tert-butyl-6-iodophenol hydrochloride

HRID 437203

Reaction equation

HRID 437203 reaction equation
[I:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[OH:12].[Cl:13]C[C:15]([NH:17]CO)=O.O>C(O)(=O)C.S(=O)(=O)(O)O>[ClH:13].[NH2:17][CH2:15][C:4]1[CH:5]=[C:6]([C:8]([CH3:9])([CH3:11])[CH3:10])[CH:7]=[C:2]([I:1])[C:3]=1[OH:12]

Participants

6

Reactant 3

HCID 962WaterHCID 62466N-Methylol-alpha-chloroacetamideHCID 101715904-Tert-butyl-2-iodophenol

Product 1

HCID 126342632-Aminomethyl-4-tert-butyl-6-iodophenol hydrochlorideYield 36.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
20 °C

Procedure

To a freshly prepared solution of 2-iodo-4-(1,1-dimethylethyl)phenol (5.5 g., 0.02 mole) in a mixture of acetic acid (27 ml.) and sulfuric acid (3 ml.) is added powdered 2-chloro-N-(hydroxymethyl)acetamide (2.5 g., 0.02 mole) with stirring at 20° C. over a 10 minute period. After 2.5 hours the orange solution is poured into water (200 ml.). The 2-chloro-N-[2-hydroxy-3-iodo-5-(1,1-dimethylethyl)benzyl]-acetamide which precipitates is collected, dried by suction and dissolved in ethanol (75 ml.). Concentrated hydrochloric acid (15 ml.) is added and the mixture is refluxed for two hours. The mixture is concentrated to one-half its original volume and allowed to cool. The resulting precipitate (1.4 g.), which is unhydrolyzed 2-chloro-N-[2-hydroxy-3-iodo-5-(1,1-dimethylethyl)benzyl]acetamide, is collected. The filtrate is concentrated to 25 ml. and, upon cooling, crude 2-aminomethyl-4-(1,1-dimethylethyl)-6-iodophenol hydrochloride (4 g.) separates which upon crystallization from a mixture of ethanol and ether affords substantially pure 2-aminomethyl-4-(1,1-dimethylethyl)-6-iodophenol hydrochloride (2.5 g.), m.p. 200°-201° (dec.).

Workup

  1. customThe 2-chloro-N-[2-hydroxy-3-iodo-5-(1,1-dimethylethyl)benzyl]-acetamide which precipitates
  2. customis collected
  3. customdried by suction
  4. dissolutiondissolved in ethanol (75 ml.)
  5. additionConcentrated hydrochloric acid (15 ml.) is added
  6. temperaturethe mixture is refluxed for two hours
  7. concentrationThe mixture is concentrated to one-half its original volume
  8. temperatureto cool
  9. customis collected
  10. concentrationThe filtrate is concentrated to 25 ml
  11. temperatureand, upon cooling
  12. customupon crystallization
  13. additionfrom a mixture of ethanol and ether

Sources & evidence

ORD record
ord-3ca19eb14bad477a832d2c618a51c427
Source dataset
uspto-grants-1977_06
Patent number
US04029816

Linked notes

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