2,2-Dimethyl-3,4-epoxy-6-cyanochroman → trans-4-(2-cyanoiminothiazolidin-3-yl)-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile

HRID 704794Notes

Reaction equation

HRID 704794 reaction equation
[O:1]1[CH:7]2[CH:2]1[C:3]([CH3:15])([CH3:14])[O:4][C:5]1[CH:11]=[CH:10][C:9]([C:12]#[N:13])=[CH:8][C:6]=12.[C:16]([N:18]=[C:19]1[NH:23][CH2:22][CH2:21][S:20]1)#[N:17]>C(N(CC)CC)C>[C:16]([N:18]=[C:19]1[N:23]([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]([CH3:15])([CH3:14])[C@H:2]2[OH:1])[CH2:22][CH2:21][S:20]1)#[N:17]

Participants

4

Reactant 2

HCID 108673602,2-Dimethyl-3,4-epoxy-6-cyanochromanHCID 178512079HCID 178512079, compound

Product 1

HCID 18643509trans-4-(2-cyanoiminothiazolidin-3-yl)-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrileYield 72.1%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3,4-epoxy-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile (0.51 g), 2-cyanoiminothiazolidine (0.64 g), and triethylamine (4.1 ml) was heated at 100° C. for 5 hours. Triethylamine was removed under reduced pressure. To the residue was added a mixture of ethyl acetate (15 ml) and water (15 ml), and the mixture was stirred for 30 minutes. The precipitate was collected by filtration and washed with ethyl acetate to give trans-4-(2-cyanoiminothiazolidin-3-yl)-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile (0.60 g).

Workup

  1. customTriethylamine was removed under reduced pressure
  2. additionTo the residue was added
  3. additiona mixture of ethyl acetate (15 ml) and water (15 ml)
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-ad0e70dd24b64a83bc8919f9a971c5e0
Source dataset
uspto-grants-1991_01
Patent number
US04988723

Reaction notes

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