Sulfuric Acid → 4-Azidobenzenesulphonic acid-[4-(2-hydroxyethyl)-phenethylamide]

HRID 1709292

Reaction equation

HRID 1709292 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:12]=[CH:11][C:7]([CH2:8][CH2:9][NH2:10])=[CH:6][CH:5]=1.C(N(CC)CC)C.[N:20]([C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1)=[N+:21]=[N-:22].S(=O)(=O)(O)O>C(Cl)Cl>[OH:1][CH2:2][CH2:3][C:4]1[CH:12]=[CH:11][C:7]([CH2:8][CH2:9][NH:10][S:29]([C:26]2[CH:25]=[CH:24][C:23]([N:20]=[N+:21]=[N-:22])=[CH:28][CH:27]=2)(=[O:30])=[O:31])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8471TriethylamineHCID 5484864-Azidobenzene-1-sulfonyl chlorideHCID 218318414-(2-Hydroxyethyl)-phenethylamine

Product 1

HCID 138260704-Azidobenzenesulphonic acid-[4-(2-hydroxyethyl)-phenethylamide]

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice cold solution of 5.5 g. (33 mmole) 4-(2-hydroxyethyl)-phenethylamine, 100 ml. methylene chloride and 3.4 g. (33 mmole) triethylamine is slowly added dropwise a solution of 7.2 g. (33 mmole) 4-azidobenzenesulphonyl chloride in 50 ml. methylene chloride. Subsequently, the reaction is allowed to continue for 1 hour with ice cooling. The reaction mixture is now shaken out twice with dilute sulphuric acid, then twice with water, dried with anhydrous sodium sulphate and finally evaporated. The residue is recrystallised twice from toluene to give 7.8 g. (64% of theory) of desired product; m.p. 90°-92° C. (recrystallised from toluene).

Workup

  1. dry with materialtwice with water, dried with anhydrous sodium sulphate
  2. customfinally evaporated
  3. customThe residue is recrystallised twice from toluene
  4. customto give 7.8 g

Sources & evidence

ORD record
ord-3c1084af816e4b858936b9721e719d58
Source dataset
uspto-grants-1990_08
Patent number
US04948809

Linked notes

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