Sodium Dithionite → HCID 13467591, compound

HRID 1085188Notes

Reaction equation

HRID 1085188 reaction equation
[Br-].[C:2]([C:5]1[CH:6]=[N+:7]([CH2:11][CH2:12][C:13](=[O:23])[NH:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:4])[NH2:3].S(S([O-])=O)([O-])=O.[Na+].[Na+]>>[C:2]([C:5]1[CH2:10][CH:9]=[CH:8][N:7]([CH2:11][CH2:12][C:13](=[O:23])[NH:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=1)(=[O:4])[NH2:3]

Participants

3

Reactant 2

HCID 24489Sodium DithioniteHCID 13467586HCID 13467586, compound

Product 1

HCID 13467591HCID 13467591, compoundYield 80.2%

Procedure

The product of Example 124 (3.78 g, 0.01 mol) was reduced according to the procedure described in Example 126 with sodium dithionite (6.96 g, 0.04 mol). After completion of the reaction, the product was extracted with ethyl acetate, washed with water, dried over anhydrous sodium sulfate, and the solvent was evaporated in vacuo. A yield of 2.4 g (80%) of the title compound was obtained as a yellowish amorphous powder, m.p. 121°-123° C. UV max (methanol) 350 nm; IR (KBr) 3430 (NH), 3260 (NH), 1670 (CO), 1630 (CO) cm-1. Anal, calc. for C17H21N3.3/4H2O: C, 65.26; H, 7.24; N, 13.43. Found: C, 65.19; H, 6.87; N, 13.61. The structure of the product was further confirmed by PMR to be: ##STR1525##

Workup

  1. customAfter completion of the reaction
  2. extractionthe product was extracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-6e934e8e5c8d4aaaad5388b2c73dcff4
Source dataset
uspto-grants-1991_04
Patent number
US05008257

Reaction notes

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