Water → trans-4-(2-cyanoiminothiazolidin-3-yl)-2,2-diethyl-3,4-dihydro-3-hydroxy-2H-1-benzopyran-6carbonitrile

HRID 704800Notes

Reaction equation

HRID 704800 reaction equation
[O:1]1[CH:7]2[CH:2]1[C:3]([CH2:16][CH3:17])([CH2:14][CH3:15])[O:4][C:5]1[CH:11]=[CH:10][C:9]([C:12]#[N:13])=[CH:8][C:6]=12.[C:18]([N:20]=[C:21]1[NH:25][CH2:24][CH2:23][S:22]1)#[N:19].O>CN(C)C=O.C(N(CC)CC)C>[C:18]([N:20]=[C:21]1[N:25]([C@@H:7]2[C:6]3[CH:8]=[C:9]([C:12]#[N:13])[CH:10]=[CH:11][C:5]=3[O:4][C:3]([CH2:16][CH3:17])([CH2:14][CH3:15])[C@H:2]2[OH:1])[CH2:24][CH2:23][S:22]1)#[N:19]

Participants

5

Reactant 3

HCID 962WaterHCID 147211883,4-epoxy-2,2-diethyl-3,4-dihydro-2H-1-benzopyran-6-carbonitrileHCID 178512079HCID 178512079, compound

Product 1

HCID 86744550trans-4-(2-cyanoiminothiazolidin-3-yl)-2,2-diethyl-3,4-dihydro-3-hydroxy-2H-1-benzopyran-6carbonitrileYield 28.9%

Reagents, catalysts & solvents 1

HCID 22056947triethylamine N,N-dimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3,4-epoxy-2,2-diethyl-3,4-dihydro-2H-1-benzopyran-6-carbonitrile (1.07 g) and 2-cyanoiminothiazolidine (0.89 g) in N,N-dimethylformamide-triethylamine (2:1, 7.5ml) was heated at 100° C. with stirring for 8 hours and 20 minutes. The reaction mixture was poured into water, extracted with ethyl acetate, washed with brine, and then dried over anhydrous magnesium sulfate. After the solution was evaporated in vacuo, the residue was purified with silica gel column chromatography using a mixture of ethyl acetate and n-hexane (1:1) as an eluent. The fractions containing the object compound were concentrated in vacuo and the residue was recrystallized from 50% aqueous acetonitrile to give trans-4-(2-cyanoiminothiazolidin-3-yl)-2,2-diethyl-3,4-dihydro-3-hydroxy-2H-1-benzopyran-6carbonitrile (0.48 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter the solution was evaporated in vacuo
  5. customthe residue was purified with silica gel column chromatography
  6. additiona mixture of ethyl acetate and n-hexane (1:1) as an eluent
  7. additionThe fractions containing the object compound
  8. concentrationwere concentrated in vacuo
  9. customthe residue was recrystallized from 50% aqueous acetonitrile

Sources & evidence

ORD record
ord-4138c89f8801466e90e54368c5730dbe
Source dataset
uspto-grants-1991_01
Patent number
US04988723

Reaction notes

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