Diethanolamine → HCID 131711114, compound

HRID 839050Notes

Reaction equation

HRID 839050 reaction equation
[NH:1]([CH2:5][CH2:6][OH:7])[CH2:2][CH2:3][OH:4].[SH:8][CH2:9][C:10]([NH:12][C:13]1[CH:14]=[C:15]([CH:23]=[CH:24][CH:25]=1)[C:16]([NH:18][CH2:19][C:20]([OH:22])=[O:21])=[O:17])=[O:11].C(CN(CC([O-])=O)CC(O)=O)N(CC(O)=O)CC([O-])=O.[Na+].[Na+].OCC[NH2+]CCO>O1CCCC1.O>[OH:4][CH2:3][CH2:2][NH2+:1][CH2:5][CH2:6][OH:7].[SH:8][CH2:9][C:10]([NH:12][C:13]1[CH:14]=[C:15]([CH:23]=[CH:24][CH:25]=1)[C:16]([NH:18][CH2:19][C:20]([O-:22])=[O:21])=[O:17])=[O:11]

Participants

7

Reactant 4

HCID 8113DiethanolamineHCID 8759EDTA disodium saltHCID 49990HCID 49990, compound2×HCID 3736299HCID 3736299, compound

Product 1

HCID 131711114HCID 131711114, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.82 ml. diethanolamine (2 g., 0.0189 mole) in 10 ml. of tetrahydrofuran is added to a mixture of N-[3-(mercaptoacetylamino)benzoyl]glycine (5 g., 0.0186 mole), 5 mg. of disodium edetate, 4 ml. of water and 40 ml. of tetrahydrofuran under an atmosphere of nitrogen during a 5-minute period at room temperature. The resulting mixture is first warmed to 40°-45° C. for 20 min. and then cooled in a dry ice-ethanol bath for 0.5 hr. to promote crystallization. Cooling is discontinued and the mixture stirred overnight under an atmosphere of nitrogen and filtered. The material collected is washed with tetrahydrofuran and then dried under vacuum over calcium chloride to provide 5.8 g., of the bis-(2-hydroxyethyl) ammonium salt of N-[3 -(mercaptoacetylamino)benzoyl]glycine, m.p. 64°-74.5° C. (dec.).

Workup

  1. temperatureThe resulting mixture is first warmed to 40°-45° C. for 20 min.
  2. temperaturecooled in a dry ice-ethanol bath for 0.5 hr
  3. customcrystallization
  4. temperatureCooling
  5. filtrationfiltered
  6. customThe material collected
  7. washis washed with tetrahydrofuran
  8. dry with materialdried under vacuum over calcium chloride
  9. customto provide 5.8 g

Sources & evidence

ORD record
ord-f99da3dcce984b6a82a2c26702dafa81
Source dataset
uspto-grants-1978_06
Patent number
US04093739

Reaction notes

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