Hydrochloric Acid → HCID 67234479, compound

HRID 882719Notes

Reaction equation

HRID 882719 reaction equation
C=O.[CH2:3]([O:10][C:11]1[CH:30]=[CH:29][C:14]([O:15][C:16]2[CH:28]=[CH:27][C:19]3[NH:20][CH2:21][CH2:22][NH:23][S:24](=[O:26])(=[O:25])[C:18]=3[CH:17]=2)=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:31]C1C(Br)=C(O)C(Br)=CC=1C1(C2C=C(Br)C(O)=C(Br)C=2C)OS(=O)(=O)C2C=CC=CC1=2.C([BH3-])#N.[Na+].Cl.C([O-])(O)=O.[Na+]>C(#N)C.O1CCOCC1.O>[CH2:3]([O:10][C:11]1[CH:30]=[CH:29][C:14]([O:15][C:16]2[CH:28]=[CH:27][C:19]3[N:20]([CH3:31])[CH2:21][CH2:22][NH:23][S:24](=[O:26])(=[O:25])[C:18]=3[CH:17]=2)=[CH:13][CH:12]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 6451Bromocresol GreenHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 67235025HCID 67235025, compound

Product 1

HCID 67234479HCID 67234479, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Procedure

Aqueous formaldehyde 37% (12.6 mmol) is added to a suspension of the product of Example 8 (2.52 mmol) in 10 ml of acetonitrile. The suspension is stirred for 1 hour at ambient temperature. A spatula tip of bromocresol green and sodium cyanoborohydride (7.56 mmol) are added in succession. The reaction mixture is brought to acid pH by adding 4N HCl solution in dioxane. The reaction mixture is stirred overnight at ambient temperature and is then neutralised by addition of 10% NaHCO3 solution. After diluting the reaction mixture with water, a precipitate forms, which is filtered off. Purification of the title product is carried out by chromatography on silica, eluting with a mixture of dichloromethane/ethyl acetate 96/4.

Workup

  1. stirringThe reaction mixture is stirred overnight at ambient temperature
  2. filtrationa precipitate forms, which is filtered off
  3. customPurification of the title product
  4. washeluting with a mixture of dichloromethane/ethyl acetate 96/4

Sources & evidence

ORD record
ord-a2f174fb53f544d0930a867cbe308584
Source dataset
uspto-grants-2012_08
Patent number
US08236790B2

Reaction notes

Loading…