Ammonium Hydroxide → HCID 86746598, compound

HRID 1613019Notes

Reaction equation

HRID 1613019 reaction equation
[OH:1][CH:2]([CH2:5][OH:6])[CH2:3][NH2:4].C(N(C(=O)C)[C:11]1[C:12]([I:29])=[C:13]([C:17]([I:28])=[C:18]([N:21]([C:25](=[O:27])[CH3:26])C(=O)C)[C:19]=1[I:20])[C:14](Cl)=[O:15])(=O)C.[OH-].[NH4+].[CH3:35][C:36]([N:38](C)C)=[O:37]>>[OH:1][CH:2]([CH2:5][OH:6])[CH2:3][NH:4][C:14](=[O:15])[CH:13]1[C:17]([I:28])=[C:18]([NH:21][C:25](=[O:27])[CH3:26])[C:19]([I:20])=[CH:11][C:12]1([NH:38][C:36](=[O:37])[CH3:35])[I:29]

Participants

5

Reactant 4

HCID 14923Ammonium HydroxideHCID 31374Dimethylacetamide2×HCID 735613-Amino-1,2-propanediolHCID 19777505HCID 19777505, compound

Product 1

HCID 86746598HCID 86746598, compound

Procedure

2,3-Dihydroxypropylamine (12.10 g, 0.0133 mole) in DMA (10 ml) was added to an ice-cold solution of 3,5-bis-diacetylamino-2,4,6-triiodobenzoyl chloride (29) (35.83 g, 0.05 mole) in DMA (50 ml), with stirring, for 10 min. The reaction mixture was stirred at room temperature, and let stir for 5 hours. Concentrated ammonium hydroxide (30 ml) was added. After 30 min, all solvents were removed in vacuo at 60° C. To the residue, 1N hydrochloric acid (50 ml) was added and the solvent removed in vacuo. The residue was mixed with ice cold water (150 ml) and the precipitate was filtered, washed with water and dried to obtain the product, N-(2',3'-dihydroxypropyl) 2,5-bis-acetylamino-2,4,6-triiodobenzamide (30), as a white solid in high yield. TLC: (silica gel): 0.36 in CHCl3 /MeOH 8:2. NMR: (DMSO-d6): COCH3 (2.02, singlet, 6H); (--CH2 -- and --CH protons (3.05 to 3.85, broad multiplet, 5H); --OH (4.2, singlet); ArCOHN-(8.4 to 8.7, broad triplet, 1H); Ar--NHCO-- (9.85 to 10.15, broad doublet, 2H).

Workup

  1. stirringThe reaction mixture was stirred at room temperature
  2. stirringlet stir for 5 hours
  3. waitAfter 30 min
  4. customall solvents were removed in vacuo at 60° C
  5. additionTo the residue, 1N hydrochloric acid (50 ml) was added
  6. customthe solvent removed in vacuo
  7. additionThe residue was mixed with ice cold water (150 ml)
  8. filtrationthe precipitate was filtered
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-de98fa1d39004106862e93e05865fc49
Source dataset
uspto-grants-1993_03
Patent number
US05191119

Reaction notes

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