2-Aminothiophenol → (4-Benzothiazol-2-ylmethyl-phenyl)-methanol

HRID 384504Notes

Reaction equation

HRID 384504 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](O)=O)=[CH:5][CH:4]=1.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[SH:20]>>[S:20]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[C:10]1[CH2:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][OH:1])=[CH:4][CH:5]=1

Participants

3

Reactant 2

HCID 87132-AminothiophenolHCID 32834984-(Hydroxymethyl)phenylacetic acid

Product 1

HCID 67205894(4-Benzothiazol-2-ylmethyl-phenyl)-methanolYield 14%

Conditions

Temperature
160 °C

Procedure

To (4-hydroxymethyl-phenyl)-acetic acid (2 g, 12 mmol) was added 2-amino-benzenethiol (13.2 g, 12 mmol) and the mixture was heated at 160° C. for 48 h. The crude residue was then partitioned between EtOAc (200 mL) and 1 N NaOH (200 mL). The organic layer was separated, washed with satd. aq. NaCl (200 mL), dried (MgSO4), filtered and concentrated. Purification by silica gel flash chromatography (0% to 80% EtOAc in hexanes) afforded the title compound as a colorless oil (0.42 g, 14%). MS (ESI): mass calcd. for C15H13NOS, 255.34; m/z found, 456.1 [M+H]+. 1H NMR (500 MHz, CDCl3): 8.00 (d, J=8.1 Hz, 1H), 7.80 (d, J=8.1 Hz, 1H), 7.48-7.45 (m, 1H), 7.39-7.28 (m, 5H), 4.71 (s, 2H), 4.44 (s, 2H).

Workup

  1. customThe crude residue was then partitioned between EtOAc (200 mL) and 1 N NaOH (200 mL)
  2. customThe organic layer was separated
  3. washwashed with satd
  4. dry with materialaq. NaCl (200 mL), dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica gel flash chromatography (0% to 80% EtOAc in hexanes)

Sources & evidence

ORD record
ord-c1a29589160a4c49a2237f5e61e326c4
Source dataset
uspto-grants-2013_02
Patent number
US08367719B2

Reaction notes

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