Ethyl 2-Aminobenzothiazole-6-carboxylate → (2-Aminobenzo[d]thiazol-6-yl)methanol

HRID 1671778Notes

Reaction equation

HRID 1671778 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([C:11](OCC)=[O:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([CH2:11][OH:12])[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

4

Reactant 2

HCID 601008Ethyl 2-Aminobenzothiazole-6-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 13821540(2-Aminobenzo[d]thiazol-6-yl)methanolYield 46.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-aminobenzo[d]thiazole-6-carboxylate (5.05 g, 22.7 mmol, 1.0 eq.) in THF (60 mL) under nitrogen at 0° C. was added LAH (1M, THF; 100 mL, 100 mmol, 4.4 eq.) over 20 min. After 6.5 h, ice was added, and the solution was stirred overnight. The precipitate was filtered and rinsed with EtOAc. The filtrate was concentrated in vacuo to give a solid which was triturated with Et2O to give (2-aminobenzo[d]thiazol-6-yl)methanol as a yellow solid (1.90 g, 46% yield).

Workup

  1. additionice was added
  2. filtrationThe precipitate was filtered
  3. washrinsed with EtOAc
  4. concentrationThe filtrate was concentrated in vacuo
  5. customto give a solid which
  6. customwas triturated with Et2O

Sources & evidence

ORD record
ord-5e5eef0aade348e99c94fc77f91ba285
Source dataset
uspto-grants-2011_08
Patent number
US07994337B2

Reaction notes

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