Acetic Acid → HCID 20531215, compound

HRID 1759579Notes

Reaction equation

HRID 1759579 reaction equation
[Cl:1][CH2:2][C:3]([NH:5][CH:6](O)[C:7]([OH:9])=[O:8])=[O:4].S(=O)(=O)(O)O.C(O)(=O)C.[S:20]1[CH2:24][CH2:23][C:22]2[CH:25]=[CH:26][CH:27]=[CH:28][C:21]1=2>O>[Cl:1][CH2:2][C:3]([NH:5][CH:6]([C:26]1[CH:27]=[CH:28][C:21]2[S:20][CH2:24][CH2:23][C:22]=2[CH:25]=1)[C:7]([OH:9])=[O:8])=[O:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 783192,3-Dihydrobenzo(b)thiopheneHCID 23257102(2-Chloroacetamido)(hydroxy)acetic acid

Product 1

HCID 20531215HCID 20531215, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-Chloroacetyl-α-hydroxyglycine (6.5 g., 0.038 mole) was added to a cold, stirred mixture of concentrated sulphuric acid (1.5 ml.) and glacial acetic acid (15 ml.) followed, after five minutes, by the dropwise addition of 2,3-dihydrobenzo(b)thiophen (98%, 4.1 g., 0.03 mole). The reaction mixture was stirred at ambient temperature for five hours, then water (75 ml.) was added to the resulting suspension and the mixture thoroughly stirred. Filtration gave a solid which was washed successively with water, diethyl ether and hexane, then dried, to afford DL-α-chloroacetamido-2,3-dihydro-5-benzo(b)thienylacetic acid (5.6 g.), m.p. 173°-175° C.

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for five hours
  2. stirringthe mixture thoroughly stirred
  3. filtrationFiltration
  4. customgave a solid which
  5. washwas washed successively with water, diethyl ether and hexane
  6. customdried

Sources & evidence

ORD record
ord-5be168416c9448a7818541a5f9996b55
Source dataset
uspto-grants-1982_07
Patent number
US04341792

Reaction notes

Loading…