Diisopropylethylamine → HCID 13914701, compound

HRID 652612Notes

Reaction equation

HRID 652612 reaction equation
Cl[C:2]1[C:15]2[C:14](=O)[C:13]3[C:8](=[C:9]([O:17][CH2:18][C:19]4[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][C:20]=4[CH3:27])[CH:10]=[CH:11][CH:12]=3)[C:7](=[O:28])[C:6]=2[C:5]([Cl:29])=[CH:4][CH:3]=1.[NH:30]([CH2:32][CH2:33][NH:34][CH2:35][CH2:36][OH:37])[NH2:31].C(N(CC)C(C)C)(C)C>C(#N)C>[Cl:29][C:5]1[CH:4]=[CH:3][C:2]2[N:30]([CH2:32][CH2:33][NH:34][CH2:35][CH2:36][OH:37])[N:31]=[C:14]3[C:13]4[C:8](=[C:9]([O:17][CH2:18][C:19]5[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][C:20]=5[CH3:27])[CH:10]=[CH:11][CH:12]=4)[C:7](=[O:28])[C:6]=1[C:15]=23

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 134138082-[(2-Hydrazinylethyl)amino]ethan-1-olHCID 14397959HCID 14397959, compound

Product 1

HCID 13914701HCID 13914701, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mechanically stirred mixture of 310 g (0.73 mol) of 1,4-dichloro-5-[(2,4,6-trimethylphenyl)methoxy]-9,10-anthracenedione, 260 g (2.19 mol) of 2-[(2-hydrazinoethyl)amino]ethanol, 381 ml (2.19 mol) of N,N-diisopropylethylamine, and 4.8 l of acetonitrile was heated at reflux for 22 hr. The cooled mixture was concentrated in vacuo to leave a residue, showing a ~1:4 ratio of 12:13, that was triturated with water. The solids were collected by filtration, washed with methanol, and dried at 220 mm/50° C./18 hr to leave 237 g (66%) of crude 13, mp 147°-158° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 22 hr
  3. concentrationThe cooled mixture was concentrated in vacuo
  4. customto leave a residue
  5. customthat was triturated with water
  6. filtrationThe solids were collected by filtration
  7. washwashed with methanol
  8. customdried at 220 mm/50° C./18 hr
  9. customto leave 237 g (66%) of crude 13, mp 147°-158° C.

Sources & evidence

ORD record
ord-5701d4640cf24796a1219df586c8668f
Source dataset
uspto-grants-1987_06
Patent number
US04672129

Reaction notes

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