Butyl 6-isocyanatohexanoate → HCID 19848120, compound

HRID 1904763Notes

Reaction equation

HRID 1904763 reaction equation
[CH:1]([O:4][C:5]([C:7]1[S:8][C:9]([C:14]([O:16][CH:17]([CH3:19])[CH3:18])=[O:15])=[C:10]([OH:13])[C:11]=1[CH3:12])=[O:6])([CH3:3])[CH3:2].[CH2:20]([O:24][C:25]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][N:32]=[C:33]=[O:34])=[O:26])[CH2:21][CH2:22][CH3:23]>C(#N)C.C1N2CCN(CC2)C1>[CH:1]([O:4][C:5]([C:7]1[S:8][C:9]([C:14]([O:16][CH:17]([CH3:19])[CH3:18])=[O:15])=[C:10]([O:13][C:33]([NH:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][C:25]([O:24][CH2:20][CH2:21][CH2:22][CH3:23])=[O:26])=[O:34])[C:11]=1[CH3:12])=[O:6])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 13836475Butyl 6-isocyanatohexanoateHCID 54703303HCID 54703303, compound

Product 1

HCID 19848120HCID 19848120, compoundYield 93.4%

Reagents, catalysts & solvents 2

HCID 9237DabcoCatalystHCID 6342AcetonitrileSolvent2×

Procedure

10.0 g of 2,5-bis-(isopropoxycarbonyl)-3-methyl-4-hydroxythiophene, 20 ml of anhydrous acetonitrile, 15 g of butoxycarbonylpentyl isocyanate (b.p. 149°-151°/ 13 millibar) and 100 mg of triethylene diamine are maintained at 100° C. for 18 hours. The mixture is diluted with 20 ml of acetonitrile. To remove the excess butoxycarbonylpentyl isocyanate, the reaction mixture is shaken three times with 50 ml of ligroin in each case. The acetonitrile phase is evaporated in vacuo. The evaporation residue is dried at 100° C./0.1 mbar. 16.3 g of 2,5-bis-(isopropoxycarbonyl)-3-methyl-4-[5-(butyloxycarbonyl)pentylaminocarbonyloxy]-thiophene are obtained as a viscous material. 1H--NMR 80 MHz CDCL3 δ-values OCH 2H m 5.0-5.5 ppm; OCH2 2H t 4.13 ppm; N--CH2 2H m 3.1-3.5 ppm; hetar-CH3 s 2.39 ppm.

Workup

  1. customTo remove the excess butoxycarbonylpentyl isocyanate
  2. customThe acetonitrile phase is evaporated in vacuo
  3. customThe evaporation residue is dried at 100° C./0.1 mbar

Sources & evidence

ORD record
ord-34fad4eeecef4f65abb1fc89f19c5695
Source dataset
uspto-grants-1989_06
Patent number
US04839381

Reaction notes

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