Triethylamine → HCID 178472678, compound

HRID 26129Notes

Reaction equation

HRID 26129 reaction equation
[O:1]=[S:2]1(=[O:20])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4](NCCCC(OCC)=O)=[N:3]1.Cl.[CH2:22]([O:24][C:25](=[O:28])[CH2:26][NH2:27])[CH3:23].C(N(CC)CC)C>O1CCOCC1>[O:1]=[S:2]1(=[O:20])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4]([NH:27][CH2:26][C:25]([O:24][CH2:22][CH3:23])=[O:28])=[N:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2723640Glycine ethyl ester, hydrochlorideHCID 178471604HCID 178471604, compound

Product 1

HCID 178472678HCID 178472678, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

15.0 g. (74.4 mM) of 3-chloro-1,2-benzisothiazole 1,1-dioxide (prepared as in Example 1), 10.4 g. (74.4 mM) of glycine ethyl ester, hydrochloride and 20.4 ml. (148.8 mM) of triethylamine are refluxed in 250 ml of dioxane for 2 hours. The dioxane is evaporated and the residue is taken up in chloroform which is washed with water (2 x) and evaporated. The residue 2-[(1,1-dioxo-1,2-benzisothiazol-3-yl)amino]acetic acid, ethyl ester is recrystallized once from 150 ml of methanol/water (1:1) and once from 200 ml. of water to give 2-[(1,1-dioxo-1,2-benzisothiazol-3-yl)amino]acetic acid, ethyl ester as yellow needles, yield 14.35 g., m.p. 166°-167°.

Workup

  1. customThe dioxane is evaporated
  2. washis washed with water (2 x)
  3. customevaporated
  4. customThe residue 2-[(1,1-dioxo-1,2-benzisothiazol-3-yl)amino]acetic acid, ethyl ester is recrystallized once from 150 ml of methanol/water (1:1) and once from 200 ml

Sources & evidence

ORD record
ord-84525733c0314d02ac153d93aa451a1a
Source dataset
uspto-grants-1979_04
Patent number
US04148798

Reaction notes

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