Triphenylphosphine → HCID 11538553, compound

HRID 1176719Notes

Reaction equation

O[C@H:2]1[CH2:7][C@@H:6]([CH3:8])[S:5][C:4]2[S:9][CH:10]=[CH:11][C:3]1=2.[CH2:12]([NH:14][S:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N+:24]([O-:26])=[O:25])(=[O:17])=[O:16])[CH3:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH-].[Na+]>C(Cl)Cl>[CH2:12]([N:14]([C@H:2]1[CH2:7][C@H:6]([CH3:8])[S:5][C:4]2[S:9][CH:10]=[CH:11][C:3]1=2)[S:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N+:24]([O-:26])=[O:25])(=[O:16])=[O:17])[CH3:13]

Participants

Conditions

Temperature: 2.5 °C

Procedure

Methylene chloride (130.5 mL), cis-4-hydroxy-5,6-dihydro-6-methyl-4-H-thieno-[2,3-b]-thiopyran (10.44 g), N-ethyl-2-nitrobenzene-sulfonamide (16.78 g) and triphenyl-phosphine (20.61 g) are mixed under nitrogen atmosphere. The mixture is cooled at 0-5° C. and diisopropyl azadicarboxylate (16.6 mL) is added, maintaining the temperature. The temperature is allowed to rise to 20-25° C. and is maintained until completing the transformation (2 hours). The resulting mixture is treated with 5% NaOH (100 mL). The resulting organic phase is vacuum distilled to dryness and the residue is chromatographed, obtaining 9.8 g of trans-4-[N-ethyl-N-(2-nitrobenzenesulfonyl)amino]-5,6-dihydro-6-methyl-4-H-thieno-[2,3-b]-thiopyran.

Workup

additiondiisopropyl azadicarboxylate (16.6 mL) is added
temperaturemaintaining the temperature
customto rise to 20-25° C.
temperatureis maintained
customthe transformation (2 hours)
distillationdistilled to dryness
customthe residue is chromatographed

Sources & evidence

ORD record: ord-663ef0aac7c24120b49feb4e7494a0bf
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842821B2

Reaction notes

Loading…