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Diethanolamine → Tris-(8-di-(2-hydroxyethyl)aminocarbonyl-2,2,6,6-tetramethylbenzo[1,2-d:5,4-d']-bis(1,3)oxathiol-4-yl)methanol

HRID 2603
Notes
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Reaction equation

HRID 2603 reaction equation
Cl[C:2]([C:4]1[C:17]2[O:16][C:15]([CH3:19])([CH3:18])[S:14][C:13]=2[C:12]([C:20]([C:41]2[C:49]3[S:50][C:51]([CH3:54])([CH3:53])[O:52][C:48]=3[C:47]([C:55](Cl)=[O:56])=[C:46]3[C:42]=2[S:43][C:44]([CH3:59])([CH3:58])[O:45]3)([C:22]2[C:30]3[S:31][C:32]([CH3:35])([CH3:34])[O:33][C:29]=3[C:28]([C:36](Cl)=[O:37])=[C:27]3[C:23]=2[S:24][C:25]([CH3:40])([CH3:39])[O:26]3)[OH:21])=[C:6]2[S:7][C:8]([CH3:11])([CH3:10])[O:9][C:5]=12)=[O:3].[OH:60][CH2:61][CH2:62][NH:63][CH2:64][CH2:65][OH:66]>C1C=CC=CC=1.O>[OH:60][CH2:61][CH2:62][N:63]([CH2:64][CH2:65][OH:66])[C:2]([C:4]1[C:17]2[O:16][C:15]([CH3:19])([CH3:18])[S:14][C:13]=2[C:12]([C:20]([C:41]2[C:49]3[S:50][C:51]([CH3:54])([CH3:53])[O:52][C:48]=3[C:47]([C:55]([N:63]([CH2:64][CH2:65][OH:66])[CH2:62][CH2:61][OH:60])=[O:56])=[C:46]3[C:42]=2[S:43][C:44]([CH3:59])([CH3:58])[O:45]3)([C:22]2[C:30]3[S:31][C:32]([CH3:35])([CH3:34])[O:33][C:29]=3[C:28]([C:36]([N:63]([CH2:64][CH2:65][OH:66])[CH2:62][CH2:61][OH:60])=[O:37])=[C:27]3[C:23]=2[S:24][C:25]([CH3:40])([CH3:39])[O:26]3)[OH:21])=[C:6]2[S:7][C:8]([CH3:11])([CH3:10])[O:9][C:5]=12)=[O:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 8113DiethanolamineHCID 88240526Tris-(8-chlorocarbonyl-2,2,6,6-tetramethyl-benzo[1,2-d:5,4-d']-bis(1,3)oxathiol-4-yl)methanol

Product 1

HCID 88242170Tris-(8-di-(2-hydroxyethyl)aminocarbonyl-2,2,6,6-tetramethylbenzo[1,2-d:5,4-d']-bis(1,3)oxathiol-4-yl)methanolYield 63.4%

Reagents, catalysts & solvents 2

HCID 241Benzene
Solvent
HCID 962WaterSolvent

Procedure

Tris-(8-chlorocarbonyl-2,2,6,6-tetramethyl-benzo[1,2-d:5,4-d']-bis(1,3)oxathiol-4-yl)methanol (0.80 g, 0.80 mmol) was dissolved in benzene (200 mL). A solution of of bis(2-hydroxyethyl)amine (8.0 g, 48 mmol) in water (200 mL) was added and after vigorous stirring overnight, the mixture was transferred to a separatory funnel. The aqueous layer was removed and the remaining solid plus the benzene layer was evaporated, dissolved in methanol and passed through a short column (neutral alumina). After elution of unwanted materials with acetonitrile, the amide was eluted with methanol. After evaporation, the product was stirred with water (50 mL) at 40° C. for 2 h and then isolated by filtration. After drying, 0.60 g (60%) of the pure amide was obtained.

Workup

  1. customthe mixture was transferred to a separatory funnel
  2. customThe aqueous layer was removed
  3. customthe remaining solid plus the benzene layer was evaporated
  4. dissolutiondissolved in methanol
  5. washAfter elution of unwanted materials with acetonitrile
  6. washthe amide was eluted with methanol
  7. customAfter evaporation
  8. stirringthe product was stirred with water (50 mL) at 40° C. for 2 h
  9. customisolated by filtration
  10. customAfter drying

Sources & evidence

ORD record
ord-b9d46f1258cf4095bcf66afa8b7bb539
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05728370

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes