Ethyl bromoacetate → HCID 9944960, compound

HRID 1819745Notes

Reaction equation

HRID 1819745 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH2:10][CH2:9][CH2:8][CH2:7][C:5]=2[N:6]=1.[Br:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]>C(O)C.CCN(CC)CC>[BrH:11].[CH2:16]([O:15][C:13](=[O:14])[CH2:12][N:6]1[C:5]2[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=2[S:3][C:2]1=[NH:1])[CH3:17]

Participants

5

Reactant 2

HCID 7748Ethyl bromoacetateHCID 180462-Amino-4,5,6,7-tetrahydrobenzothiazole

Product 1

HCID 9944960HCID 9944960, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-amino-4,5,6,7-tetrahydrobenzothiazole (2.296 g, 14.9 mmol) and ethyl bromoacetate (2.747 g, 16.4 mmol) was refluxed in ethanol (50 mL) containing 3 drops of Et3N for 90 minutes. The reaction mixture was concentrated to half volume in vacuo and the resulting precipitate was filtered and rinsed with cold ethanol, then ether to give a white powder in 79% yield: mp 222-224° C.; 1H-NMR (DMSO-d6) 1.25 (t, 3H), 1.74 (d, 4H), 2.39 (s, 2H), 2.52 (m, 2H), 4.22 (q, 2H), 4.95 (s, 2H), 9.67 (s, 2H); Anal. C11H17Br1N2O2S (C, H, N); HR-MS (EI) m/z 240.0931 (M+).

Workup

  1. concentrationThe reaction mixture was concentrated to half volume in vacuo
  2. filtrationthe resulting precipitate was filtered
  3. washrinsed with cold ethanol
  4. customether to give a white powder in 79% yield

Sources & evidence

ORD record
ord-bc6384a3227d4c83ae011059b3d2c6f7
Source dataset
uspto-grants-2009_10
Patent number
US07601846B2

Reaction notes

Loading…