Phosphorus oxide (P4O10) → HCID 11352260, compound

HRID 2266952Notes

Reaction equation

[C:1]1([S:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH:14][C:15]([N:17]2[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][C:29](=[O:36])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:19][CH2:18]2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)(Cl)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>>[CH:5]1[C:6]2[C:15]([N:17]3[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][C:29](=[O:36])[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH2:19][CH2:18]3)=[N:14][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[S:7][C:1]=2[CH:2]=[CH:3][CH:4]=1

Participants

Reactant 3

HCID 14812Phosphorus oxide (P4O10)

HCID 24813Phosphorus oxychloride

HCID 11432126HCID 11432126, compound

Product 1

HCID 11352260HCID 11352260, compound

Conditions

Temperature: 90 °C

Procedure

Benzoic acid 2-{2-[4-(2-phenylsulfanyl-phenylcarbamoyl)piperazin-1-yl]-ethoxy}-ethyl ester (2 g, 3.96 mmol), phosphorus oxychloride (15 ml) and phosphorus pentoxide (2 g) were charged into a reaction flask. Then the mixture was stirred at 90° C. for 19 h. Phosphorus oxychloride was evaporated in vacuo. Dichloromethane (20 ml) and ice-water (20 ml) were added to the residue. NaHCO3 was added until the pH was 7-8. The organic phase was separated, washed with saturated NaCl-water (10 ml), dried with Na2SO4 and evaporated. Yield of benzoic acid 2-[2-(4-dibenzo[b,f][1,4]-thiazepin-11-yl-piperazin-1-yl]-ethoxy]-ethyl ester 1.53 g.

Workup

customPhosphorus oxychloride was evaporated in vacuo
additionDichloromethane (20 ml) and ice-water (20 ml) were added to the residue
additionNaHCO3 was added until the pH was 7-8
customThe organic phase was separated
washwashed with saturated NaCl-water (10 ml)
dry with materialdried with Na2SO4
customevaporated

Sources & evidence

ORD record: ord-969ddb80d73c48e795faa4b0adb5af25
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858777B2

Reaction notes

Loading…