Butyl 6-isocyanatohexanoate → HCID 19848120, compound

HRID 845251Notes

Reaction equation

HRID 845251 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.

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-b83ad34bed224b22ae0cba75b9997c82
Source dataset
uspto-grants-1988_07
Patent number
US04757085

Reaction notes

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