Methylamine → HCID 69069293, compound

HRID 734369Notes

Reaction equation

HRID 734369 reaction equation
[CH3:1][N:2]([C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]=[C:15]([CH3:20])[C:14]2([CH3:22])[CH3:21])C(=O)COCC(O)=O.CN(C1C=CC2N=C(C)SC=2C=1)C(=O)COCC(O)=O.CN.C1(=O)OC(=O)COC1>C(Cl)(Cl)Cl>[CH3:1][NH:2][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]=[C:15]([CH3:20])[C:14]2([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 6329MethylamineHCID 782321,4-Dioxane-2,6-dioneHCID 69071765HCID 69071765, compoundHCID 69072849HCID 69072849, compound

Product 1

HCID 69069293HCID 69069293, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The yield was 86%, yellow solid. 1H NMR (500 MHz, CDCl3): δ 1.34 (s, 6H, 2×CH3), 2.29 (s, 3H, CH3), 2.94 (s, 3H, NCH3), 3.52 (s, 1H, NH), 6.5-7.5 (m, 3H, aromatic ring). ESI-MS: 189 (MH+). {2-[Methyl(2,3,3-trimethyl-3H-indol-5-yl)amino]-2-oxoethoxy}-acetic Acid (20) and {2-[Methyl(2-methyl-1,3-benzothiazol-6-yl)-amino]-2-oxoethoxy}acetic Acid (21). N-Methylamine from the previous synthesis (1.0 mmol) was dissolved in 20 mL of chloroform. A 1.1 mmol sample of diglycolic anhydride was added, and the mixture was stirred under reflux for 2 h. After cooling, the solvent was evaporated. The solid was recrystallized from acetone to give pure acids.

Workup

  1. temperatureunder reflux for 2 h
  2. temperatureAfter cooling
  3. customthe solvent was evaporated
  4. customThe solid was recrystallized from acetone
  5. customto give pure acids

Sources & evidence

ORD record
ord-3b505a28f5f34b8ab4cb6f047b23e73a
Source dataset
uspto-grants-2009_09
Patent number
US07592188B2

Reaction notes

Loading…