Triethylamine → HCID 88417474, compound

HRID 1608753Notes

Reaction equation

HRID 1608753 reaction equation
[S:1]([C:5]1[CH:6]=[CH:7][C:8]2[C:9]([CH:28]=1)=[CH:10][CH:11]=[C:12]1[C:16]=2[NH+:15]([CH2:17]CCCS(O)(=O)=O)[CH:14]([CH3:25])[C:13]1([CH3:27])[CH3:26])([OH:4])(=[O:3])=[O:2].C(N(CC)CC)C>C(OC(=O)C)(=O)C>[C:8]1([CH3:16])[CH:9]=[CH:28][C:5]([S:1]([O-:4])(=[O:2])=[O:3])=[CH:6][CH:7]=1.[CH3:17][NH+:15]1[C:16]2[C:12](=[CH:11][CH:10]=[C:9]3[CH:28]=[CH:5][CH:6]=[CH:7][C:8]3=2)[C:13]([CH3:27])([CH3:26])[CH:14]1[CH3:25]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 131718922HCID 131718922, compound

Product 1

HCID 88417474HCID 88417474, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

N-[5-(Phenylamino)-2-hydroxy-2,5-pentadienylidene]aniline monohydrochloride (15.0 g, 0.05 mol), 7-sulfo-2,3,3-trimethyl-(4-sulfobutyl)-1H-benzindolium, inner salt [NKX-1632 from the Japanese Institute of Photosensitizing Dyes], (41.3 g, 0.1 mol) and 300 ml acetic anhydride were stirred together at ambient temperature. Triethylamine (20.2 g, 0.2 mol) was added and the mixture was stirred 80 minutes at ambient temperature. The mixture was filtered and poured into 2000 ml stirred ethyl acetate. The ethyl acetate was filtered away and the solid reslurried twice in ethyl acetate. After filtering and vacuum drying, the yield was 61.79 g of dye, mp 177°-195° C., λmax (methanol)=789 nm (ε=215,000).

Workup

  1. filtrationThe mixture was filtered
  2. additionpoured into 2000 ml
  3. stirringstirred ethyl acetate
  4. filtrationThe ethyl acetate was filtered away
  5. filtrationAfter filtering
  6. customvacuum drying

Sources & evidence

ORD record
ord-9b53b72e286e4e449dd5d4767dba6b7c
Source dataset
uspto-grants-1995_03
Patent number
US05397690

Reaction notes

Loading…