Water → 2-Aminomethyl-4-(1-methylethyl)-6-iodophenol hydrochloride

HRID 437207Notes

Reaction equation

HRID 437207 reaction equation
[I:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[OH:11].[Cl:12]C[C:14]([NH:16]CO)=O.O>C(O)(=O)C.S(=O)(=O)(O)O>[ClH:12].[NH2:16][CH2:14][C:4]1[CH:5]=[C:6]([CH:8]([CH3:9])[CH3:10])[CH:7]=[C:2]([I:1])[C:3]=1[OH:11]

Participants

6

Reactant 3

HCID 962WaterHCID 62466N-Methylol-alpha-chloroacetamideHCID 126521002-Iodo-4-(propan-2-yl)phenol

Product 1

HCID 203268632-Aminomethyl-4-(1-methylethyl)-6-iodophenol hydrochlorideYield 42.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
20 °C

Procedure

2-Iodo-4-(1-methylethyl)phenol (13.1 g., 0.05 mole) is dissolved in a mixture of acetic acid (50 ml.) and 96% sulfuric acid (5 ml.) and powdered 2-chloro-N-(hydroxymethyl)acetamide (6.15 g., 0.05 mole) is added during 10 minutes with stirring at 20° C. The solution is stirred for 2.5 hours and then added to 300 ml. of water. The crude solid (18 g.) is collected and refluxed in ethanol (25 ml.)-hydrochloric acid (10 ml.) for 2 hours. The solid (7.5 g.) that separates on cooling, namely 2-aminomethyl-4-(1-methylethyl)-6-iodophenol hydrochloride, is purified by crystallization from ethanol 12N-hydrochloric acid (7:3) to obtain 2-aminomethyl-4-(1-methylethyl)-6-iodophenol hydrochloride (7 g.), m.p. 211°-212° C. (dec.).

Workup

  1. additionis added during 10 minutes
  2. stirringThe solution is stirred for 2.5 hours
  3. additionadded to 300 ml
  4. customThe crude solid (18 g.) is collected
  5. temperaturerefluxed in ethanol (25 ml.)-hydrochloric acid (10 ml.) for 2 hours
  6. temperatureon cooling
  7. customnamely 2-aminomethyl-4-(1-methylethyl)-6-iodophenol hydrochloride, is purified by crystallization from ethanol 12N-hydrochloric acid (7:3)

Sources & evidence

ORD record
ord-40f15b3967114cf38617f2b80f836d31
Source dataset
uspto-grants-1977_06
Patent number
US04029816

Reaction notes

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