Water → Methyl 5-amino-3-(methanesulfonyl)-1,2-thiazole-4-carboxylate

HRID 1178705Notes

Reaction equation

HRID 1178705 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]([S:14]([CH3:17])(=[O:16])=[O:15])=[N:7][S:8][C:9]=1S(C)(=O)=O)=[O:4].C[N:19](C=O)C.O>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[C:6]([S:14]([CH3:17])(=[O:16])=[O:15])=[N:7][S:8][C:9]=1[NH2:19])=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 58975480Methyl 3,5-di(methanesulfonyl)-1,2-thiazole-4-carboxylate

Product 1

HCID 58975483Methyl 5-amino-3-(methanesulfonyl)-1,2-thiazole-4-carboxylateYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 3 neck flask fitted with a condenser, compound 16 (1 g, 3.33 mmol) is dissolved in THF (20 mL) and DMF (2 mL) and warmed to 50° C. Ammonia gas is then bubbled into the reaction mixture for 16 hrs. The solvent is then removed in vacuo to provide a crude solid. Water is added to the solid and the mixture is then filtered and washed with water (2×) followed by methylene chloride (5 mL×2) to provide 17 (588 mg, 75%) as a yellow powder. 1H NMR (d6 DMSO): δ 8.11 (2H, br. s), 3.74 (3H, s), 3.30 (3H, s). LRMS (M+): 237.1, (M−): 235.0.

Workup

  1. customIn a 3 neck flask fitted with a condenser
  2. customAmmonia gas is then bubbled into the reaction mixture for 16 hrs
  3. customThe solvent is then removed in vacuo
  4. customto provide a crude solid
  5. filtrationthe mixture is then filtered
  6. washwashed with water (2×)

Sources & evidence

ORD record
ord-3c78850efdc6471481d698a40fea4483
Source dataset
uspto-grants-2007_10
Patent number
US07276602B2

Reaction notes

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