Dimethyl Sulfate → HCID 20309676, compound

HRID 1763283Notes

Reaction equation

HRID 1763283 reaction equation
[C:1]([C:4]1[C:5]([I:22])=[C:6]([C:16]([I:21])=[C:17]([NH2:20])[C:18]=1[I:19])[NH:7][C:8](=[O:15])[CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])([OH:3])=[O:2].[OH-].[Na+].S(OC)(O[CH3:29])(=O)=O>CC(C)=O>[C:1]([C:4]1[C:5]([I:22])=[C:6]([C:16]([I:21])=[C:17]([NH2:20])[C:18]=1[I:19])[N:7]([CH3:29])[C:8](=[O:15])[CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 6497Dimethyl Sulfate2×HCID 14798Sodium Hydroxide2×HCID 20309625HCID 20309625, compound

Product 1

HCID 20309676HCID 20309676, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 26.0 g. of 3'-carboxy-5'-amino-2',4',6'-triiodoglutaranilic acid (Example 21, part d) in 100 ml. of 10% aqueous sodium hydroxide cooled in an ice bath was added 8 ml. of dimethyl sulfate in acetone. After 3 hours of stirring an additional 15 ml. of 10% sodium hydroxide and 2 ml. of dimethyl sulfate were added and the mixture stirred 3 hours longer. The reaction mixture was acidified, and the product collected and recrystallized from acetic acid to give 3'-carboxy-5'-amino-2',4',6'-triiodo-N-methylglutaranilic acid, pale gray catalyst, m.p. 218°-220° C. (dec.).

Workup

  1. additionwas added 8 ml
  2. stirringthe mixture stirred 3 hours longer
  3. customthe product collected
  4. customrecrystallized from acetic acid

Sources & evidence

ORD record
ord-136400bd47944c0f8fc3555c4d7f7aa1
Source dataset
uspto-grants-1978_09
Patent number
US04111937

Reaction notes

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