Dimethylformamide → trans-4-(2-cyanoiminothiazolidin-3-yl)-3,4-dihydro-3-hydroxy-6-mesyl-2,2-dimethyl-2H-1-benzopyran

HRID 1030212Notes

Reaction equation

HRID 1030212 reaction equation
[O:1]1[CH:7]2[CH:2]1[C:3]([CH3:17])([CH3:16])[O:4][C:5]1[CH:11]=[CH:10][C:9]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:8][C:6]=12.[C:18]([N:20]=[C:21]1[NH:25][CH2:24][CH2:23][S:22]1)#[N:19].C(N(CC)CC)C.CN(C)C=O>O>[C:18]([N:20]=[C:21]1[N:25]([C@@H:7]2[C:6]3[CH:8]=[C:9]([S:12]([CH3:15])(=[O:14])=[O:13])[CH:10]=[CH:11][C:5]=3[O:4][C:3]([CH3:17])([CH3:16])[C@H:2]2[OH:1])[CH2:24][CH2:23][S:22]1)#[N:19]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 142103893,4-dihydro-3,4-epoxy-6-mesyl-2,2-dimethyl-2H-1-benzopyranHCID 178512079HCID 178512079, compound

Product 1

HCID 86745665trans-4-(2-cyanoiminothiazolidin-3-yl)-3,4-dihydro-3-hydroxy-6-mesyl-2,2-dimethyl-2H-1-benzopyranYield 71.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3,4-dihydro-3,4-epoxy-6-mesyl-2,2-dimethyl-2H-1-benzopyran (1.5 g), 2-(cyanoimino)-thiazolidine (1.1 g), triethylamine (3 ml) and N,N-dimethylformamide (6 ml) was stirred at 100° C. for 5 hours. After cooling, the reaction mixture was poured into water. The precipitate was collected by filtration, washed well with water and dried in vacuo to give trans-4-(2-cyanoiminothiazolidin-3-yl)-3,4-dihydro-3-hydroxy-6-mesyl-2,2-dimethyl-2H-1-benzopyran (1.6 g).

Workup

  1. temperatureAfter cooling
  2. filtrationThe precipitate was collected by filtration
  3. washwashed well with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-c526317784ad45119d085d37471d424c
Source dataset
uspto-grants-1992_04
Patent number
US05104890

Reaction notes

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