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Carbon Dioxide → 5-[[4-[(6-Hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromen-2-yl)methoxy]phenyl]methyl]-2-imino-1,3-thiazolidin-4-one

HRID 1589677
Notes
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Reaction equation

HRID 1589677 reaction equation
C([O:4][C:5]1[C:6]([CH3:34])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH:27](Cl)[C:28](OCC)=[O:29])=[CH:22][CH:21]=1)([CH3:17])[CH2:9][CH2:8]2)(=O)C.[NH2:35][C:36]([NH2:38])=[S:37].S1(CCCC1)(=O)=O.Cl.C(=O)(O)[O-].[Na+].C(=O)=O>O.C(O)(=O)C>[OH:4][C:5]1[C:6]([CH3:34])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH:27]3[S:37][C:36](=[NH:35])[NH:38][C:28]3=[O:29])=[CH:22][CH:21]=1)([CH3:17])[CH2:9][CH2:8]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 6

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 31347SulfolaneHCID 516892Sodium BicarbonateHCID 2723790ThioureaHCID 13605832HCID 13605832, compound

Product 1

HCID 140341589
5-[[4-[(6-Hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromen-2-yl)methoxy]phenyl]methyl]-2-imino-1,3-thiazolidin-4-one
Yield 25.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 9.6 g of ethyl 3-[4-(6-acetoxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)phenyl]-2-chloropropionate, 1.8 g of thiourea and 11 ml of sulfolane was reacted for 80 minutes under a nitrogen stream at 115°-120° C. Subsequently, a mixture of 90 ml of acetic acid, 30 ml of concentrated hydrochloric acid and 15 ml of water was added to this, and the resulting mixture was further heated for 12 hours at 85°-90° C. 27 g of sodium bicarbonate were added to this reaction mixture, and, once evolution of carbon dioxide had ceased, the solvent was distilled off. A 10:1 by volume mixture of benzene and ethyl acetate was added to the residue, and the crude product was washed with a mixture of equal volumes of a saturated aqueous solution of sodium bicarbonate and water. The white powder produced was removed by filtration and washed again with water. It was then recrystallized from acetone to give 2.2 g of 5 -[4-(6-hydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]-2-iminothiazolidin-4-one, melting at 205°-207° C.

Workup

  1. customwas reacted for 80 minutes under a nitrogen stream at 115°-120° C
  2. additionwas added to this, and the resulting mixture
  3. temperaturewas further heated for 12 hours at 85°-90° C
  4. distillationthe solvent was distilled off
  5. additionA 10:1 by volume mixture of benzene and ethyl acetate
  6. additionwas added to the residue
  7. washthe crude product was washed with a mixture of equal volumes of a saturated aqueous solution of sodium bicarbonate and water
  8. customThe white powder produced
  9. customwas removed by filtration
  10. washwashed again with water
  11. customIt was then recrystallized from acetone

Sources & evidence

ORD record
ord-0f4d20c51b3d4603b05235753d319fce
Source dataset
uspto-grants-1986_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04572912

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes