HCID 13286112, compound → HCID 131715899, compound

HRID 1194761Notes

Reaction equation

HRID 1194761 reaction equation
[N:1]([O-])=O.[Na+].[ClH:5].[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][S:14]([NH:17][CH2:18][CH:19]=[CH2:20])(=[O:16])=[O:15])=[CH:9][CH:8]=1>O.Cl>[ClH:5].[NH:6]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][S:14]([NH:17][CH2:18][CH:19]=[CH2:20])(=[O:16])=[O:15])=[CH:9][CH:8]=1)[NH2:1]

Participants

5

Reactant 2

HCID 13286112HCID 13286112, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 131715899HCID 131715899, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A solution of sodium nitrite (1.06 g) in water (2.5 ml) was added dropwise to a stirred suspension of the product from stage (b) (3.5 g) in 5N hydrochloric acid (28 ml) between -8° and -3° under nitrogen and stirring was continued at ca -3° for 80 min. The mixture was filtered, and the clear yellow filtrate was added dropwise from an ice-cooled, jacketed dropping funnel to a stirred solution of stannous chloride dihydrate (17.5 g) in concentrated hydrochloric acid (17.5 ml) between -2° and +1° over 35 min. After warming up to 10° over 15 min, the mixture was filtered, and the residue was washed with concentrated hydrochloric acid (4×30 ml) and dry ether (4×30 ml) and dried to give the title compound as a very pale yellow solid (2.44 g), m.p. 163°-166°, containing 5% inorganic material.

Workup

  1. filtrationThe mixture was filtered
  2. additionthe clear yellow filtrate was added dropwise from an ice-
  3. temperaturecooled
  4. customto a stirred solution of stannous chloride dihydrate (17.5 g) in concentrated hydrochloric acid (17.5 ml) between -2° and +1°
  5. customover 35 min
  6. temperatureAfter warming up to 10° over 15 min
  7. filtrationthe mixture was filtered
  8. washthe residue was washed with concentrated hydrochloric acid (4×30 ml) and dry ether (4×30 ml)
  9. customdried

Sources & evidence

ORD record
ord-6c8c15314a924f90a1c49c5e38e5eebf
Source dataset
uspto-grants-1989_03
Patent number
US04816470

Reaction notes

Loading…