Sulfolane → HCID 9846824, compound

HRID 1589681Notes

Reaction equation

HRID 1589681 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[CH3:15])[O:11][C:10]([CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH:26](Cl)[C:27](OCC)=[O:28])=[CH:21][CH:20]=1)([CH3:16])[CH2:9][CH2:8]2)(=[O:3])[CH3:2].[NH2:33][C:34](N)=[S:35].S1(CCCC1)(=O)=[O:38]>>[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[CH3:15])[O:11][C:10]([CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH:26]3[S:35][C:34](=[O:38])[NH:33][C:27]3=[O:28])=[CH:21][CH:20]=1)([CH3:16])[CH2:9][CH2:8]2)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 31347SulfolaneHCID 2723790ThioureaHCID 20245704HCID 20245704, compound

Product 1

HCID 9846824HCID 9846824, compound

Conditions

Temperature
120 °C

Procedure

The reactions described in Example 1(a) were repeated, except that 1.5 g of ethyl 3-[4-(6-acetoxy-2,7-dimethylchroman-2-ylmethoxy)phenyl]-2-chloropropionate, 300 mg of thiourea and 2 ml of sulfolane were heated at 120° C. for 2 hours. The reaction mixture was then purified by adding diethyl ether to the reaction mixture, and distilling off the solvent to leave a residue. This residue was purified by column chromatography through silica gel eluted first with a 9:1 by volume mixture of benzene and ethyl acetate, to give the title compound.

Workup

  1. customThe reaction mixture was then purified
  2. additionby adding diethyl ether to the reaction mixture
  3. distillationdistilling off the solvent
  4. customto leave a residue
  5. customThis residue was purified by column chromatography through silica gel
  6. washeluted first with a 9:1 by volume mixture of benzene and ethyl acetate

Sources & evidence

ORD record
ord-939d92b40457425ea0d80d48871e948e
Source dataset
uspto-grants-1986_02
Patent number
US04572912

Reaction notes

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