Benzene → HCID 53649741, compound

HRID 1029975Notes

Reaction equation

HRID 1029975 reaction equation
[C:1]1(C)C=[CH:5][C:4](S(O)(=O)=O)=[CH:3][CH:2]=1.[C:12]([NH:31][C:32]1[S:33][CH:34]=[C:35]([C:37](=[N:43][OH:44])[C:38]([O:40][CH2:41][CH3:42])=[O:39])[N:36]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1C=CC=CC=1.[OH2:51]>O1C=CCCC1.C(N(CC)CC)C>[C:12]([NH:31][C:32]1[S:33][CH:34]=[C:35]([C:37](=[N:43][O:44][CH:5]2[CH2:4][CH2:3][CH2:2][CH2:1][O:51]2)[C:38]([O:40][CH2:41][CH3:42])=[O:39])[N:36]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 241BenzeneHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 6802348Ethyl 2-(2-tritylamino-4-thiazolyl)-2-hydroxyiminoacetate

Product 1

HCID 53649741HCID 53649741, compound

Reagents, catalysts & solvents 2

HCID 80803,4-dihydro-2H-pyranSolventHCID 8471TriethylamineSolvent

Procedure

2.4 g of p-toluene sulfonic acid were added to a mixture of 5.6 g of the product of Step A in 56 ml of redistilled dihydropyran in an ice bath and the mixture was then stirred for an hour while the temperature returned to room temperature. The mixture was poured into a mixture of 100 ml of benzene, 100 ml of water and 2 ml of triethylamine and the organic phase was decanted, was washed with water, dried and vacuum filtered. The filter was rinsed with benzene and the filtrate was evaporated to dryness. The residue was taken up in isopropyl ether and crystallization was induced. The mixture was stored overnight in a refrigerator and was then vacuum filtered. The product was rinsed with isopropyl ether to obtain 4.42 g of the syn isomer of ethyl 2-(2-tritylamino-4-thiazolyl)-2-tetrahydropyranyloxyimino-acetate melting at 184° C.

Workup

  1. customreturned to room temperature
  2. customthe organic phase was decanted
  3. washwas washed with water
  4. customdried
  5. filtrationvacuum filtered
  6. washThe filter was rinsed with benzene
  7. customthe filtrate was evaporated to dryness
  8. customcrystallization
  9. filtrationvacuum filtered
  10. washThe product was rinsed with isopropyl ether

Sources & evidence

ORD record
ord-0b0563f1d74c41ed8e2a84604cba2f41
Source dataset
uspto-grants-1992_04
Patent number
US05103012

Reaction notes

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