Ethanolamine → HCID 131711113, compound

HRID 839049Notes

Reaction equation

HRID 839049 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].[SH:5][CH2:6][C:7]([NH:9][C:10]1[CH:11]=[C:12]([CH:20]=[CH:21][CH:22]=1)[C:13]([NH:15][CH2:16][C:17]([OH:19])=[O:18])=[O:14])=[O:8].C(CN(CC([O-])=O)CC(O)=O)N(CC(O)=O)CC([O-])=O.[Na+].[Na+]>O1CCCC1.O>[OH:2][CH2:1][CH2:3][NH3+:4].[SH:5][CH2:6][C:7]([NH:9][C:10]1[CH:11]=[C:12]([CH:20]=[CH:21][CH:22]=1)[C:13]([NH:15][CH2:16][C:17]([O-:19])=[O:18])=[O:14])=[O:8]

Participants

6

Reactant 3

HCID 700EthanolamineHCID 8759EDTA disodium saltHCID 49990HCID 49990, compound

Product 1

HCID 131711113HCID 131711113, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

A solution 1.13 ml. of ethanolamine (1.15 g., 0.0188 mole) and 10 ml. of tetrahydrofuran is added to a suspension of N-[3-(mercaptoacetylamino)benzoyl]glycine (5 g., 0.0186 mole), 5 mg. of disodium edetate, 6 ml. of water, and 40 ml. of tetrahydrofuran. Warming the mixture to 40°-45° C. provides a clear solution which is first diluted with 200 ml. of tetrahydrofuran, then cooled in a dry ice-acetone bath to promote crystallization and subsequently stirring for a period of 16 hrs. at room temperature. The precipitated material formed is collected, washed with tetrahydrofuran and dried over calcium chloride to afford 5.7 g., (93% yield) of N-[3-(mercaptoacetylamino)benzoyl]glycine 2-hydroxyethyl ammonium salt, m.p. 144.0°-160.0° C. (dec.).

Workup

  1. temperatureWarming the mixture to 40°-45° C.
  2. customprovides a clear solution which
  3. additionis first diluted with 200 ml
  4. customcrystallization
  5. customat room temperature
  6. customThe precipitated material formed
  7. customis collected
  8. washwashed with tetrahydrofuran
  9. dry with materialdried over calcium chloride
  10. customto afford 5.7 g

Sources & evidence

ORD record
ord-41c6c68b7b584086818f8434d7f2faf9
Source dataset
uspto-grants-1978_06
Patent number
US04093739

Reaction notes

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