Hydroxyamine hydrochloride → HCID 22617350, compound

HRID 1955952Notes

Reaction equation

HRID 1955952 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([S:12][CH3:13])=S.[O:14]1[CH:19]=CSC=[N:15]1.Cl.NO>C(N(CC)CC)C>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[S:12][CH2:13][CH2:19][O:14][N:15]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 14573950Methyl 1,3-benzothiazole-2-carbodithioateHCID 218648921,4,2-Oxathiazine

Product 1

HCID 22617350HCID 22617350, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Methyl 2-benzothiazolecarbodithioate (37 g, 0.16 mol) was converted to 1,4,2-oxathiazine using hydroxylamine hydrochloride (13.2 g) and triethylamine (33 ml) as described in Example 4. The ethyl acetate extract of the product was washed successively with diluted hydrochloric acid (2N), water, 5% sodium hydroxide and water. Evaporation of the solvent left a solid residue which was recrystallized from ethanol/ethyl acetate to 5,6-dihydro-3-(2-benzothiazolyl)-1,4,2-oxathiazine (18.0 g, mp 150°-151° C.) Found C 50.68, H 3.27, N 11.78, C10 H8N2OS2 requires C 50.85, H 3.39, N 11.80.

Workup

  1. extractionThe ethyl acetate extract of the product
  2. washwas washed successively with diluted hydrochloric acid (2N), water, 5% sodium hydroxide and water
  3. customEvaporation of the solvent
  4. waitleft a solid residue which
  5. customwas recrystallized from ethanol/ethyl acetate to 5,6-dihydro-3-(2-benzothiazolyl)-1,4,2-oxathiazine (18.0 g, mp 150°-151° C.) Found C 50.68, H 3.27, N 11.78

Sources & evidence

ORD record
ord-72273fb2591544a8baf76a1d5f031b83
Source dataset
uspto-grants-1998_07
Patent number
US05777110

Reaction notes

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