N-bromobutanimide → Methyl 2-amino-4,5,6,7-tetrahydro-1,3-benzothiazole-6-carboxylate

HRID 704586Notes

Reaction equation

HRID 704586 reaction equation
C[Si](C)(C)O[C:4]1[CH2:9][CH2:8][CH:7]([C:10]([O:12][CH3:13])=[O:11])[CH2:6][CH:5]=1.BrN1C(=O)CCC1=O.[NH2:24][C:25]([NH2:27])=[S:26]>O1CCCC1>[NH2:27][C:25]1[S:26][C:5]2[CH2:6][CH:7]([C:10]([O:12][CH3:13])=[O:11])[CH2:8][CH2:9][C:4]=2[N:24]=1

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 2723790ThioureaHCID 15101119Methyl 4-[(trimethylsilyl)oxy]cyclohex-3-ene-1-carboxylate

Product 1

HCID 15101120Methyl 2-amino-4,5,6,7-tetrahydro-1,3-benzothiazole-6-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The procedure of M. E. Jung, et al, Journal of the American Chemical Society, Volume 103, pages 6177-6185 (1981), is followed to prepare (±)-methyl 4-[(trimethylsilyl)oxy]-3-cyclohexene-1-carboxylate. A solution of 100 g of this compound in 500 ml of dry tetrahydrofuran is cooled in an ice bath under nitrogen and treated sequentially with N-bromosuccinimide (92.91 g) and 20 minutes later with thiourea (39.73 g). The mixture is refluxed under nitrogen for two hours. The solvent is removed in vacuo and the residue is partitioned between chloroform and a dilute solution of ammonium hydroxide. The organic phase is washed with brine and dried over magnesium sulfate. Evaporation of the solvent gives 82.7 g of the title compound; mp 148°-168° C.

Workup

  1. temperatureThe mixture is refluxed under nitrogen for two hours
  2. customThe solvent is removed in vacuo
  3. customthe residue is partitioned between chloroform
  4. washThe organic phase is washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-b8ac20c7e62e43b09965320e69072210
Source dataset
uspto-grants-1991_01
Patent number
US04988699

Reaction notes

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