Ammonium Hydroxide → 2-Amino-thiazole-5-carboxylic acid ethyl ester

HRID 854334Notes

Reaction equation

HRID 854334 reaction equation
[CH2:1]1[C:6](=[O:7])N(Br)C(=O)[CH2:2]1.[NH2:9][C:10]([NH2:12])=[S:11].[OH-:13].[NH4+].O1CCO[CH2:17][CH2:16]1.O>>[NH2:9][C:10]1[S:11][C:1]([C:6]([O:7][CH2:16][CH3:17])=[O:13])=[CH:2][N:12]=1

Participants

5

Reactant 4

HCID 14923Ammonium HydroxideHCID 67184N-bromobutanimideHCID 2723790ThioureaHCID 218864351,4-Dioxane--water (1/1)

Product 1

HCID 3146282-Amino-thiazole-5-carboxylic acid ethyl ester

Conditions

Temperature
80 °C

Procedure

To a mixture of B-ethoxyacrylic acid ethyl ester (2.0 g, 13.9 mmol) in 1:1 dioxane/water (15 mL) at −10°0 C. was added NBS (2.72 g, 15.3 mmol). Thiourea (1.06 g, 13.9 mmol) was added and the mixture was heated to 80° C. and stirred for 1.5 h. The reaction mixture was cooled to 0° C. and 5 mL of saturated ammonium hydroxide was added. A precipitate formed in 15 min. The solid was filtered, washed with water and dried under vacuum, yielding a light orange solid.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. customA precipitate formed in 15 min
  3. filtrationThe solid was filtered
  4. washwashed with water
  5. customdried under vacuum
  6. customyielding a light orange solid

Sources & evidence

ORD record
ord-28e552c801664036ac43afc3242afdec
Source dataset
uspto-grants-2007_08
Patent number
US07259157B2

Reaction notes

Loading…