Acetic Anhydride → HCID 19819829, compound

HRID 1031143Notes

Reaction equation

HRID 1031143 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]([NH2:15])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:16]([O:19]C(=O)C)(=[O:18])[CH3:17]>N1C=CC=CC=1>[C:16]([O:19][NH:15][CH:7]([C:3]1[S:4][CH:5]=[CH:6][C:2]=1[CH3:1])[CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)(=[O:18])[CH3:17]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 19819810HCID 19819810, compound

Product 1

HCID 19819829HCID 19819829, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 10 g (0.047 mol) of α-(3-methyl-2-thienyl)benzeneethanamine in 50 ml of pyridine at ambient temperature was added dropwise 6.6 ml (0.07 mol) of acetic anhydride. Mixture was allowed to stand overnight, diluted with 500 ml of ETOAC, washed with 1N HCl until acidic, water, brine and dried. The resulting dark oil obtained from concentration of the organics was purified by chromatography on silica gel to give 8.2 g ( 0.032 mol) of N-acetoxy-α-(3-methyl-2-thienyl)benzeneethanamine as a light brown solid. To a stirred suspension of this solid in 45 ml of THF at 0° C. was added dropwise 64 ml (0.064 mol) of a 1.M solution of borane in THF. The resulting mixture was allowed to warm to ambient temperature and stirred overnight. The reaction was quenched by carefully adding 100 ml of 6N HCl and was then warmed at 75° C. for 40 hours. The mixture was cooled, made basic with 50% aqueous NaOH, and extracted with CH2Cl2 (3×200 ml). The organic extracts were combined, washed with water, brine, and dried. The resulting oil obtained from concentration of organics was dissolved in 50 ml isopropanol and made acidic with hydrochlorinated isopropanol. The white solid was collected by filtration and dried giving 5. g of product as a white solid (mp 226°-228° C.).

Workup

  1. additiondiluted with 500 ml of ETOAC
  2. washwashed with 1N HCl until acidic, water, brine
  3. customdried
  4. customThe resulting dark oil obtained from concentration of the
  5. customorganics was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-5bcfd794245e4177927a56b7479c5237
Source dataset
uspto-grants-1992_04
Patent number
US05109017

Reaction notes

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