Sulfolane → HCID 140341593, compound

HRID 1589683Notes

Reaction equation

HRID 1589683 reaction equation
[C:1]([O:4][C:5]1[C:6]([CH3:37])=[C:7]2[C:12](=[C:13]([O:17][CH3:18])[C:14]=1[O:15][CH3:16])[O:11][C:10]([CH2:20][CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH:30](Cl)[C:31](OCC)=[O:32])=[CH:25][CH:24]=1)([CH3:19])[CH2:9][CH2:8]2)(=[O:3])[CH3:2].[NH2:38][C:39]([NH2:41])=[S:40].S1(CCCC1)(=O)=O>>[C:1]([O:4][C:5]1[C:6]([CH3:37])=[C:7]2[C:12](=[C:13]([O:17][CH3:18])[C:14]=1[O:15][CH3:16])[O:11][C:10]([CH2:20][CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH:30]3[S:40][C:39](=[NH:38])[NH:41][C:31]3=[O:32])=[CH:25][CH:24]=1)([CH3:19])[CH2:9][CH2:8]2)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 31347SulfolaneHCID 2723790ThioureaHCID 20245668HCID 20245668, compound

Product 1

HCID 140341593HCID 140341593, compound

Procedure

The procedure described in Example 1(a) was repeated, except that 558 mg of ethyl 3-{4-[2-(6-acetoxy-7,8-dimethoxy-2,5-dimethylchroman-2-yl)ethoxy]phenyl}-2-chloropropionate, 100 mg of thiourea and 12 ml of sulfolane were heated at 110°-115° C. for 3.5 hours. The product was subsequently treated as described in Example 1(a), except that the crude product, in the form of an oil, was purified by column chromatography through silica gel, eluted with a 20:1 by volume mixture of ethyl acetate and methanol, to give the title compound, softening at 103°-110° C.

Workup

  1. temperaturewere heated at 110°-115° C. for 3.5 hours
  2. additionThe product was subsequently treated
  3. customwas purified by column chromatography through silica gel
  4. washeluted with a 20:1 by volume mixture of ethyl acetate and methanol

Sources & evidence

ORD record
ord-310d1a23d22049568154f62b0e5a66a8
Source dataset
uspto-grants-1986_02
Patent number
US04572912

Reaction notes

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