Sulfolane → [2-[[4-[(2-imino-4-oxo-1,3-thiazolidin-5-yl)methyl]phenoxy]methyl]-2,5,7,8-tetramethyl-4-oxo-3H-chromen-6-yl] acetate

HRID 1589695Notes

Reaction equation

HRID 1589695 reaction equation
[C:1]([O:4][C:5]1[C:6]([CH3:35])=[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][C:8]2=[O:34])(=[O:3])[CH3:2].[NH2:36][C:37]([NH2:39])=[S:38].S1(CCCC1)(=O)=O>>[C:1]([O:4][C:5]1[C:6]([CH3:35])=[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:38][C:37](=[NH:36])[NH:39][C:28]3=[O:29])=[CH:22][CH:21]=1)([CH3:17])[CH2:9][C:8]2=[O:34])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 31347SulfolaneHCID 2723790ThioureaHCID 13649224Ethyl 3-[4-(6-acetoxy-2,5,7,8-tetramethyl-4-oxochroman-2-ylmethoxy)phenyl]-2-chloropropionate

Product 1

HCID 140341611[2-[[4-[(2-imino-4-oxo-1,3-thiazolidin-5-yl)methyl]phenoxy]methyl]-2,5,7,8-tetramethyl-4-oxo-3H-chromen-6-yl] acetate

Procedure

A mixture of 2.0 g of ethyl 3-[4-(6-acetoxy-2,5,7,8-tetramethyl-4-oxochroman-2-ylmethoxy)phenyl]-2-chloropropionate (prepared as described in Preparation 45), 0.62 g of thiourea, and 3.1 g of sulfolane was heated at 120°-125° C. for 7 hours under a nitrogen stream. The reaction mixture was extracted with benzene and then the benzene was distilled off from the extract. Water was then added to the residue and the oily layer was separated. The oily layer was subjected to silica gel column chromatography [successively with an eluent of (1) a 2:1 by volume mixture of n-hexane and ethyl acetate, (2) ethyl acetate, and (3) a 1:1 by volume mixture of ethyl acetate and ethanol] to yield 5-[4-(6-acetoxy-2,5,7,8-tetramethyl-4-oxochroman-2-ylmethoxy)benzyl]-2-iminothiazolidin-4-one in a yield of 0.74 g. This was further purified by recrystallization from ethyl acetate, to give the purified title compound melting at was 218°-222° C.

Workup

  1. temperaturewas heated at 120°-125° C. for 7 hours under a nitrogen stream
  2. extractionThe reaction mixture was extracted with benzene
  3. distillationthe benzene was distilled off from the extract
  4. additionWater was then added to the residue
  5. customthe oily layer was separated
  6. additionby volume mixture of n-hexane and ethyl acetate, (2) ethyl acetate, and (3) a 1:1
  7. additionby volume mixture of ethyl acetate and ethanol]

Sources & evidence

ORD record
ord-c7ea6d8c29b546a8a00f3a61d2597c52
Source dataset
uspto-grants-1986_02
Patent number
US04572912

Reaction notes

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