Formamide → HCID 10075956, compound

HRID 1613510Notes

Reaction equation

HRID 1613510 reaction equation
[CH:1]([NH2:3])=O.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:5].Cl[CH2:19][C:20]([C:22]1[CH:49]=[CH:48][C:25]([O:26][CH2:27][CH2:28][CH2:29][O:30][C:31]2[CH:44]=[CH:43][C:34]3[CH2:35][CH2:36][CH:37]([C:39]([O:41][CH3:42])=[O:40])[O:38][C:33]=3[C:32]=2[CH2:45][CH2:46][CH3:47])=[C:24]([CH2:50][CH2:51][CH3:52])[C:23]=1[O:53][CH3:54])=O.C(=O)([O-])[O-].[Mg+2]>O1CCOCC1.C(OCC)C>[CH3:54][O:53][C:23]1[C:24]([CH2:50][CH2:51][CH3:52])=[C:25]([CH:48]=[CH:49][C:22]=1[C:20]1[N:3]=[CH:1][S:5][CH:19]=1)[O:26][CH2:27][CH2:28][CH2:29][O:30][C:31]1[CH:44]=[CH:43][C:34]2[CH2:35][CH2:36][CH:37]([C:39]([O:41][CH3:42])=[O:40])[O:38][C:33]=2[C:32]=1[CH2:45][CH2:46][CH3:47]

Participants

7

Reactant 4

HCID 713FormamideHCID 11029Magnesium CarbonateHCID 14817Phosphorus sulfide (P2S5)HCID 10030026HCID 10030026, compound

Product 1

HCID 10075956HCID 10075956, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent2×

Procedure

Formamide (24 mL, 0.69 mmol), phosphorus pentasulfide (54 mg, 0.123 mmol) and 4 mL of dioxane were refluxed for 30 min. Methyl 7-[3-[4-(2-chloro-1-oxoethyl)-3-methoxy-2-propylphenoxy]propoxy]-3,4-dihydro-8-propyl-2H-1-benzopyran-2-carboxylate (30 mg, 0.056 mmol) in 0.5 mL dioxane was added along with 50 mg magnesium carbonate, and the mixture was refluxed for 18 hr. The reaction mixture was poured into ethyl ether/0.5N sodium hydroxide, and the ether layer was washed with brine, dried over sodium sulfate, and concentrated. Flash chromatography of the concentrate using 10:1 hexane/ethyl acetate as eluant provided the product (30 mg, 0.055 mmol, 99% yield). High resolution mass spectrum, m/e 539.2335 (calculated for C30H37SO6N, 539.2341).

Workup

  1. temperaturethe mixture was refluxed for 18 hr
  2. washthe ether layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-63c66d6fd936407d8ef6258e0ce504ef
Source dataset
uspto-grants-1993_03
Patent number
US05192782

Reaction notes

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