Diisopropyl Ether → HCID 19989812, compound

HRID 973441Notes

Reaction equation

HRID 973441 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[CH3:9][O:10][C:11]1[CH:12]=[C:13]([C:17](=[CH2:21])[C:18]([OH:20])=[O:19])[CH:14]=[CH:15][CH:16]=1.C(OC(C)C)(C)C>C(O)C>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH2:21][CH:17]([C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([O:10][CH3:9])[CH:12]=1)[C:18]([OH:20])=[O:19]

Participants

5

Reactant 3

HCID 7914Diisopropyl EtherHCID 87132-AminothiophenolHCID 14838159HCID 14838159, compound

Product 1

HCID 19989812HCID 19989812, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
95 °C

Procedure

7.6 ml of aminothiophenol were added to a solution of 8.9 g of the product of Step C and 130 ml of ethanol and the solution was stirred for 90 minutes at 95° C. and left to return to ambient temperature. The ethanol was eliminated under reduced pressure and 50 ml of isopropyl ether were added. Crystallization was started to obtain 7.2 of the expected product which was separated off and dried at 80° C. under reduced pressure. After chromatography of the mother liquors on silica (eluant: ethyl acetate-cyclohexane 1-1), 710 mg of pure product were obtained (Rf=0.16) which after crystallization from ether melted at 128° C.

Workup

  1. waitleft
  2. customto return to ambient temperature
  3. additionwere added
  4. customCrystallization

Sources & evidence

ORD record
ord-09abe03895964a99b00a2c61c56631c8
Source dataset
uspto-grants-1991_11
Patent number
US05063225

Reaction notes

Loading…