Sodium Bicarbonate → HCID 19785836, compound

HRID 1252236Notes

Reaction equation

HRID 1252236 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]([NH:7][CH2:8][CH2:9][N:10]([C:20]1[N:25]=[C:24]([N:26]([CH2:36][CH2:37][NH:38][C:39]([O:41][CH2:42][CH2:43][OH:44])=[O:40])[CH2:27][CH2:28][NH:29][C:30]([O:32][CH2:33][CH2:34][OH:35])=[O:31])[N:23]=[C:22](Cl)[N:21]=1)[CH2:11][CH2:12][NH:13][C:14]([O:16][CH2:17][CH2:18][OH:19])=[O:15])=[O:6].[C:46](=[O:49])([OH:48])[O-].[Na+]>C(O)CO>[OH:1][CH2:2][CH2:3][O:4][C:5]([NH:7][CH2:8][CH2:9][N:10]([CH2:11][CH2:12][NH:13][C:14]([O:16][CH2:17][CH2:18][OH:19])=[O:15])[C:20]1[N:25]=[C:24]([N:26]([CH2:36][CH2:37][NH:38][C:39]([O:41][CH2:42][CH2:43][OH:44])=[O:40])[CH2:27][CH2:28][NH:29][C:30]([O:32][CH2:33][CH2:34][OH:35])=[O:31])[N:23]=[C:22]([N:10]([CH2:9][CH2:8][NH:7][C:5]([O:4][CH2:3][CH2:2][OH:1])=[O:6])[CH2:11][CH2:12][NH:13][C:46]([O:48][CH2:18][CH2:17][OH:16])=[O:49])[N:21]=1)=[O:6]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 57314960HCID 57314960, compound

Product 1

HCID 19785836HCID 19785836, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
115 °C

Procedure

To 6.7 g of (I) (Example 1, TECT) were added 2.8 g HEC, 0.84 g sodium bicarbonate and 25 g ethylene glycol. The reaction mixture was then heated to 115° C. in an oil bath for 4 hours, after which most of the HEC had reacted with TECT as indicated by amine titration of the reaction mixture. Ethylene glycol was distilled off under reduced pressure. The residue was poured into methanol. Separated solids were filtered and recrystallized from methanol. Yield 5.6 g (60% of theoretical), m.p. 192° C. The nmr and fab mass spectra confirmed the product to be of FORMULA II: ##STR21##

Workup

  1. customafter which most of the HEC had reacted with TECT
  2. distillationEthylene glycol was distilled off under reduced pressure
  3. additionThe residue was poured into methanol
  4. customSeparated solids
  5. filtrationwere filtered
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-72228894ec7644e9960de2fc7ec4775f
Source dataset
uspto-grants-1988_05
Patent number
US04742118

Reaction notes

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