Hydrochloric Acid → HCID 135838380, compound

HRID 2309274Notes

Reaction equation

HRID 2309274 reaction equation
O.[OH:2][C:3]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[S:6](=[O:14])(=[O:13])[N:5]([CH3:15])[C:4]=1[C:16]1[NH:20][N:19]=[N:18][N:17]=1.O[C:22]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2S(=O)(=O)N(C)C=1C1NN=NN=1.C(=O)([O-])[O-].[K+].[K+].C(Br)C1C=CC=CC=1.Cl>CN(C)C=O>[OH:2][C:3]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[S:6](=[O:13])(=[O:14])[N:5]([CH3:15])[C:4]=1[C:16]1[N:20]=[N:19][N:18]([CH2:22][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:26]=2)[N:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178479980HCID 178479980, compound

Product 1

HCID 135838380HCID 135838380, compoundYield 144.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-hydroxy-2-methyl-3-(5-tetrazolyl)-2H-1,2-benzothiazine 1,1-dioxide hemihydrate (18.0 g) and potassium carbonate (4.32 g), in N,N-dimethylformamide (63 ml) was added benzylbromide (7.81 ml). After being stirred for 16 hours at room temperature, the mixture was poured into 1N HCl (500 ml) with stirring. The resulting solids were filtered off and washed with water (100 ml) and then with petroleum ether (50 ml). The wet solids were recrystallized from toluene (150 ml) to give 4-hydroxy-3-[(2-benzyl)tetrazol-5-yl]-2-methyl-1,2-benzothiazine 1,1-dioxide (16.70 g). The mother liquor contains the said compound and its 1-benzyl isomer. It was concentrated to an oil (6.03 g), which was treated with acetic anhydride (30 ml) at 110° C. for 1.5 hours, concentrated and crystallized in toluene (30 ml), to afford 4-acetoxy-3-[(2-benzyl)-tetrazol-5-yl]-2-methyl-1,2-benzothiazine 1,1-dioxide (1.31 g). The resulting mother liquor was concentrated to a viscous oil, diluted with toluene (10 ml) and seeded. The resulting crystals were filtered off and recrystallized from toluene (24 ml) to give 4-acetoxy-[(1-benzyl)tetrazol-5-yl]-2-methyl-1,2-benzothiazine 1,1-dioxide (0.602 g).

Workup

  1. stirringwith stirring
  2. filtrationThe resulting solids were filtered off
  3. washwashed with water (100 ml)
  4. customThe wet solids were recrystallized from toluene (150 ml)

Sources & evidence

ORD record
ord-225f5d07c14c432f9d3a5120e12e54b4
Source dataset
uspto-grants-1987_09
Patent number
US04694080

Reaction notes

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