Hydroxyamine hydrochloride → HCID 22617350, compound

HRID 841854Notes

Reaction equation

HRID 841854 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, C10H8N2OS2 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, C10H8N2OS2

Sources & evidence

ORD record
ord-aca7d54aa3a84332b308447803f0fff8
Source dataset
uspto-grants-2002_04
Patent number
US06372297B1

Reaction notes

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