Oxalyl chloride → HCID 14151761, compound

HRID 1722631Notes

Reaction equation

HRID 1722631 reaction equation
[S:1]1[C:5]([C:6](Cl)=[O:7])=[CH:4][C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2.S1C(C(O)=O)=CC2C=CC=CC1=2.C(Cl)(=O)C(Cl)=O.[NH2:31][CH:32]([P:41](=[O:48])([O:45][CH2:46][CH3:47])[O:42][CH2:43][CH3:44])[P:33](=[O:40])([O:37][CH2:38][CH3:39])[O:34][CH2:35][CH3:36]>C(Cl)Cl.CN(C)C1C=CN=CC=1.C(OCC)(=O)C.N1C=CC=CC=1>[S:1]1[C:5]([C:6]([NH:31][CH:32]([P:33](=[O:40])([O:34][CH2:35][CH3:36])[O:37][CH2:38][CH3:39])[P:41](=[O:48])([O:45][CH2:46][CH3:47])[O:42][CH2:43][CH3:44])=[O:7])=[CH:4][C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2

Participants

9

Reactant 4

HCID 65578Oxalyl chlorideHCID 95864Benzo(b)thiophene-2-carboxylic acidHCID 142384Benzo[b]thiophene-2-carbonyl ChlorideHCID 2773808Tetraethyl aminomethylenediphosphonate

Product 1

HCID 14151761HCID 14151761, compound

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-benzo[b]thiophenecarbonyl chloride prepared from 2-benzo[b]thiophenecarboxylic acid (356 mg) and oxalyl chloride (0.35 ml) in methylene chloride (2 ml) was added dropwise a mixture of tetraethyl (aminomethylene)bis(phosphonate) (606 mg), pyridine (316 mg) and trace amounts of 4-(dimethylamino)pyridine in methylene chloride (8 ml) at 5° C. The mixture was stirred for 2 hours at ambient temperature followed by the addition of ethyl acetate. The mixture was washed with water, 1N hydrochloric acid, saturated aqueous solution of sodium bicarbonate and brine successively. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was treated with diisopropyl ether to give tetraethyl [(2-benzo[b]thiophenecarboxamido)methylene]bis(phosphonate) (790 mg) as a white powder which was recrystallized from a mixture of ethyl acetate and n-hexane.

Workup

  1. additionwas added dropwise
  2. customat 5° C
  3. washThe mixture was washed with water, 1N hydrochloric acid, saturated aqueous solution of sodium bicarbonate and brine successively
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionThe residue was treated with diisopropyl ether

Sources & evidence

ORD record
ord-5c4012131973463b9706dc0719cefe06
Source dataset
uspto-grants-1989_08
Patent number
US04857513

Reaction notes

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