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

HRID 1452945Notes

Reaction equation

HRID 1452945 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-9a0b5597c4114ba481cda1ce523ee9b9
Source dataset
uspto-grants-2009_01
Patent number
US07473784B2

Reaction notes

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