Dichloromethane → HCID 9902605, compound

HRID 226177Notes

Reaction equation

HRID 226177 reaction equation
[C:1]1([NH:7][S:8]([C:11]2[CH:12]=[C:13]([C:17]#[C:18]/[CH:19]=[CH:20]/[C:21]([OH:23])=O)[CH:14]=[CH:15][CH:16]=2)(=[O:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)Cl.Cl.[NH2:28][OH:29].C([O-])(O)=O.[Na+]>O>[OH:29][NH:28][C:21](=[O:23])/[CH:20]=[CH:19]/[C:18]#[C:17][C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([S:8](=[O:10])(=[O:9])[NH:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:12]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 22492410HCID 22492410, compound

Product 1

HCID 9902605HCID 9902605, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of (E)-5-(3-phenylsulfamoylphenyl)pent-2-en-4-ynoic acid (56a) (0.25 g 0.77 mmol) in methylene chloride (5 ml) oxalyl chloride (0.42 g 3.1 mmol) was added. The resultant mixture was stirred for 1 hour at ambient temperature and the solvents were removed under reduced pressure. The crude product (57a) was dissolved in acetonitrile (5 ml) and the obtained solution to a mixture of hydroxylamine hydrochloride (0.3 g, 4.3 mmol) and NaHCO3 (0.3 g, 3.6 mmol) in water (8 ml) was added. The reaction mixture was stirred for 10 min. and the product was extracted with ethyl acetate (30 ml). The extract was washed with 10% Na2CO3, and the aqueous phase was acidified with 3% HCl. The precipitate was filtered and dried to give the title compound (0.12 g, (46%). M.p 88-90° C. 1H NMR (DMSO-d6, HMDSO) δ: 6.41 (1H, d, J=15.8 Hz, CH); 6.82 (1H, d, J=15.8 Hz, CH); 6.92-7.41 (5H, m, C6H5); 7.47-8.01 (4H, m, C6H4); 8.94-11.21 (3H, br s, NH, NH, OH). Anal. Calcd for C17H14N2O4S*0.4H2O: C 58.58, H 4.27, N 8.01. Found: C 58.12, H 4.03, N 7.80.

Workup

  1. customthe solvents were removed under reduced pressure
  2. dissolutionThe crude product (57a) was dissolved in acetonitrile (5 ml)
  3. additionwas added
  4. extractionthe product was extracted with ethyl acetate (30 ml)
  5. washThe extract was washed with 10% Na2CO3
  6. filtrationThe precipitate was filtered
  7. customdried

Sources & evidence

ORD record
ord-5d84791e34ee4b5db4324979c6e0284d
Source dataset
uspto-grants-2009_07
Patent number
US07557140B2

Reaction notes

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