Diethanolamine → HCID 131711114, compound

HRID 2163250Notes

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

Conditions

Temperature: 42.5 °C

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

temperaturecooled in a dry ice-ethanol bath for 0.5 hr
customcrystallization
temperatureCooling
filtrationfiltered
customThe material collected
washis washed with tetrahydrofuran
dry with materialdried under vacuum over calcium chloride
customto provide 5.8 g

Sources & evidence

ORD record: ord-52962a5d57bc46a7871300015cc15bb0
Source dataset: uspto-grants-1979_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04132803

Reaction notes

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