Ethanethiol → HCID 53862387, compound

HRID 1598432Notes

Reaction equation

HRID 1598432 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]2[C:4]=1[CH2:5][CH:6]([C:15](O)=O)[O:7][CH2:8]2.C(N1[CH:29]=[CH:28]N=C1)(N1C=CN=C1)=O.C([SH:32])C>C1COCC1>[CH2:28]([C:15]([CH:6]1[CH2:5][C:4]2[C:9](=[C:10]([O:13][CH3:14])[CH:11]=[CH:12][C:3]=2[O:2][CH3:1])[CH2:8][O:7]1)=[S:32])[CH3:29]

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 682631,1'-CarbonyldiimidazoleHCID 18932693HCID 18932693, compound

Product 1

HCID 53862387HCID 53862387, compoundYield 59.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5,8-dimethoxy-3-carboxyisochroman (300 mg, 1.26 mmol) in THF (6 ml) was stirred with 1,1'-carbonyldiimidazole (225 mg, 1.386 mmol) at room temperature for 30 minutes. More THF (6 ml) was added to dilute the forming suspension. After one hour, ethanethiol (103 μl, 1.40 mmol) was added and the mixture was stirred for 18 hours at room temperature. Solvent was evaporated and the crude titled product was chromatographed (hex:EtOAc=4:1) to give desired product as a solid (200 mg, m.p. 99.2° C).

Workup

  1. additionto dilute the forming suspension
  2. customSolvent was evaporated
  3. customthe crude titled product was chromatographed (hex:EtOAc=4:1)

Sources & evidence

ORD record
ord-2d3c586313a24b67a08cf4b33ed090b2
Source dataset
uspto-grants-1998_04
Patent number
US05736523

Reaction notes

Loading…