Sodium Bicarbonate → HCID 178483720, compound

HRID 424549Notes

Reaction equation

HRID 424549 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:10]([CH2:11][CH2:12][CH2:13][N:14]([CH3:22])[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:9][CH2:8][S:7][C:6]=2[CH:23]=1.I.[S:25]1[CH:29]=[CH:28][CH:27]=[C:26]1[C:30](SC)=[NH:31].C([O-])(O)=O.[Na+]>C(O)C>[CH3:22][N:14]([CH2:13][CH2:12][CH2:11][N:10]1[CH2:9][CH2:8][S:7][C:6]2[CH:23]=[C:2]([NH:1][C:30]([C:26]3[S:25][CH:29]=[CH:28][CH:27]=3)=[NH:31])[CH:3]=[CH:4][C:5]1=2)[C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 59144118HCID 59144118, compoundHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178483720HCID 178483720, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of tert-butyl 3-(7-amino-2H-benzo[b][1,4]thiazin-4(3H)-yl)propyl(methyl)carbamate (0.52 g, 1.541 mmol) in dry ethanol (20 mL) was treated with methyl thiophene-2-carbimidothioate hydroiodide (0.879 g, 3.08 mmol) at room temperature and stirred over night (18 hours). The reaction was basified with saturated NaHCO3 solution (50 mL), and the product was extracted into CH2Cl2 (2×25 mL). The combined CH2Cl2 layers were washed with brine (20 mL) and dried (Na2SO4). The solvent was evaporated, and the crude material was purified by column chromatography (2:98 (2 M NH3 in MeOH):CH2Cl2) on silica gel to obtain the title product (0.60 g, 87%) as a solid. ESI-MS (m/z, %): 447 (MH+, 100).

Workup

  1. extractionthe product was extracted into CH2Cl2 (2×25 mL)
  2. washThe combined CH2Cl2 layers were washed with brine (20 mL)
  3. dry with materialdried (Na2SO4)
  4. customThe solvent was evaporated
  5. customthe crude material was purified by column chromatography (2:98 (2 M NH3 in MeOH):CH2Cl2) on silica gel

Sources & evidence

ORD record
ord-c842984bcf2048a7970d1df9eabcca63
Source dataset
uspto-grants-2012_01
Patent number
US08106043B2

Reaction notes

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