Ethanol → HCID 23452879, compound

HRID 1277586Notes

Reaction equation

HRID 1277586 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:13]=[C:12]([OH:14])[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[C:5]=1[N+:15]([O-:17])=[O:16].C(O)C.CN(C)C(=N)N(C)C.[CH2:30](I)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47]>O>[N+:15]([C:5]1[C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:11][C:12]([O:14][CH2:47][CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH3:30])=[CH:13][C:4]=1[C:3]([O:2][CH3:1])=[O:18])([O-:17])=[O:16]

Participants

6

Reactant 4

HCID 702EthanolHCID 124021-IodooctadecaneHCID 664601,1,3,3-TetramethylguanidineHCID 23452882HCID 23452882, compound

Product 1

HCID 23452879HCID 23452879, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 19.5 g. of dimethyl-5-hydroxy-2-nitroisophthalate in 150 ml. of dry ethanol are added 8.8 g. of tetramethylguanidine, followed by 29.1 g. of octadecyliodide. The mixture is refluxed for 16 hr., cooled, and poured into 700 ml. of water. The precipitate is collected and washed well with water. The dried crude product is triturated with methanol. The insoluble solid is collected, giving 32.6 g. of product, m.p. 65°-68° C., which is used without further purification.

Workup

  1. temperatureThe mixture is refluxed for 16 hr
  2. temperature, cooled
  3. additionpoured into 700 ml
  4. customThe precipitate is collected
  5. washwashed well with water
  6. customThe dried crude product
  7. customis triturated with methanol
  8. customThe insoluble solid is collected
  9. customgiving 32.6 g
  10. customof product, m.p. 65°-68° C., which is used without further purification

Sources & evidence

ORD record
ord-19158a9a0a604e0da669b087461b3a4e
Source dataset
uspto-grants-1981_07
Patent number
US04278598

Reaction notes

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