Hydrochloric Acid → HCID 19838412, compound

HRID 2259550Notes

Reaction equation

HRID 2259550 reaction equation
[C:1]([CH2:4][N:5]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12][N:11]([CH2:17][C:18]([OH:20])=[O:19])[CH2:10][CH2:9][N:8]([CH2:21][C:22]([OH:24])=[O:23])[CH2:7][CH2:6]1)([OH:3])=[O:2].[OH-].C([N+](C)(C)C)C1C=CC=CC=1.Cl[CH2:38][C:39]([NH2:41])=[O:40].Cl>O>[C:1]([CH2:4][N:5]1[CH2:16][CH2:15][N:14]([CH2:38][C:39](=[O:40])[NH2:41])[CH2:13][CH2:12][N:11]([CH2:17][C:18]([OH:20])=[O:19])[CH2:10][CH2:9][N:8]([CH2:21][C:22]([OH:24])=[O:23])[CH2:7][CH2:6]1)([OH:3])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6580ChloroacetamideHCID 66854Benzyltrimethylammonium hydroxideHCID 1078301,4,7-Tris(carboxymethyl)-1,4,7,10-tetraazacyclododecane

Product 1

HCID 19838412HCID 19838412, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

The pH of a solution of 1.40 g of 1,4,7-tris(carboxymethyl)-1,4,7,10-tetraazacyclododecane in about 4 ml water was adjusted to 9.5 using 40% aqueous benzyltrimethylammonium hydroxide. To the resulting solution was added 412 mg α-chloroacetamide. The temperature was increased to 80° C. and base was added as necessary to maintain the pH at 9.5-10. After 3 hours the solution was cooled to room temperature and acidified to pH 3 with concentrated HCl. The resulting solution was evaporated under reduced pressure to a colorless sludge. The mixture was taken up in about 25 ml MeOH and re-evaporated. The thick residue was triturated with a 1:1 mixture of acetone and ethanol to provide a granular solid and colorless solution. The solid was collected by filtration, washed with acetone/ethanol followed by acetone and finally ether, then dried in a vacuum oven at 50° for 2 hours. Obtained was 1.54 g of the title compound as a colorless powder. The product was twice crystallized from ethanol/water.

Workup

  1. additionbase was added as necessary
  2. temperatureto maintain the pH at 9.5-10
  3. temperatureAfter 3 hours the solution was cooled to room temperature
  4. customThe resulting solution was evaporated under reduced pressure to a colorless sludge
  5. customre-evaporated
  6. customThe thick residue was triturated with a 1:1 mixture of acetone and ethanol
  7. customto provide a granular solid and colorless solution
  8. filtrationThe solid was collected by filtration
  9. washwashed with acetone/ethanol
  10. customdried in a vacuum oven at 50° for 2 hours
  11. customObtained

Sources & evidence

ORD record
ord-0d79a9943a084ad7a460e9849bd605ec
Source dataset
uspto-grants-1995_12
Patent number
US05474756

Reaction notes

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