Ammonium Hydroxide → HCID 22598077, compound

HRID 1760257Notes

Reaction equation

HRID 1760257 reaction equation
[C:1]([N:8]1C=CN=C1)(N1C=CN=C1)=[O:2].[Si:13]([O:20][CH:21](O)[CH2:22][C:23]1[S:24][C:25]([Cl:28])=[CH:26][CH:27]=1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].[OH-:30].[NH4+]>ClCCl>[Si:13]([O:20][CH2:21][CH:22]([C:23]1[S:24][C:25]([Cl:28])=[CH:26][CH:27]=1)[O:30][C:1](=[O:2])[NH2:8])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 22598093HCID 22598093, compound

Product 1

HCID 22598077HCID 22598077, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Imidazole (0.45 g) was added to a solution of 1(5-chloro-2-thienyl)-1,2-ethanediol (1.0 g, 5.6 mmol) and tert-butyldimethylsilyl chloride (0.80 g) in N,N-dimethylformamide (5 ml) at 5°. The reaction mixture was allowed to come to room temperature and stirred 1 hour, extracted with ethyl acetate, washed with 0.5N aqueous hydrochloric acid, saturated sodium bicarbonate and brine. The extracts were dried over sodium sulfate, filtered, concentrated in vacuo. 1-tert-butyldimethylsilyloxy-2-(5-chloro-2-thienyl)ethan-1-ol (1.14 g) was obtained as a colorless oil after a chromatographic purification. 1,1′-Carbonyldiimidazole (0.95 g) was added to a solution of the foregoing alcohol (1.14 g 3.9 mmol) in dichloromethane (20 mL) at 5°. The reaction mixture was allowed to come to room temperature and stirred 1 hour. Ammonium hydroxide (equivalent to 28% ammonia in water, 10 ml) was added at 5°. The reaction mixture was stirred for 1 hour at room temperature, extracted with ethyl acetate, washed with 0.5N aqueous hydrochloric acid, saturated sodium bicarbonate and brine. The extracts were dried over sodium sulfate, filtered, concentrated in vacuo. 1-tert-butyldimethylsilyloxy-2-(5-chloro-2-thienyl)-2-carbamoyloxyethane (0.47 g) was obtained as a colorless oil after a chromatographic purification.

Workup

  1. customafter a chromatographic purification
  2. customto come to room temperature
  3. stirringThe reaction mixture was stirred for 1 hour at room temperature
  4. extractionextracted with ethyl acetate
  5. washwashed with 0.5N aqueous hydrochloric acid, saturated sodium bicarbonate and brine
  6. dry with materialThe extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3416c435163f460ab6fc2030a9af4572
Source dataset
uspto-grants-2005_01
Patent number
US06841569B2

Reaction notes

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