Formic Acid → HCID 54086924, compound

HRID 1029533Notes

Reaction equation

HRID 1029533 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([S:16][CH2:17][CH2:18][C:19]([NH:21][NH2:22])=[O:20])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])[CH3:3].[CH:23](O)=[O:24]>>[CH:23]([NH:22][NH:21][C:19](=[O:20])[CH2:18][CH2:17][S:16][C:7]1[CH:8]=[C:9]([C:12]([CH3:13])([CH3:14])[CH3:15])[C:10]([OH:11])=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[CH:6]=1)=[O:24]

Participants

3

Reactant 2

HCID 284Formic AcidHCID 19609556HCID 19609556, compound

Product 1

HCID 54086924HCID 54086924, compoundYield 89%

Procedure

A solution of 3-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]propanoic acid hydrazide (0.70 g, 2.16 mmol) in 96% formic acid (5.6 mL) is stirred overnight. The reaction mixture is concentrated in vacuo, diluted with ethyl acetate and washed once with a saturated solution of sodium bicarbonate, twice with water, and once with brine. Drying the organic phase over magnesium sulfate and evaporation gives an oil which is crystallized from ethyl acetate/hexane to afford 0.68 g (89%) of 3-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]propanoic acid 2-formylhydrazide, mp 158.0°-159.0° C.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. additiondiluted with ethyl acetate
  3. washwashed once with a saturated solution of sodium bicarbonate, twice with water
  4. customDrying the organic phase
  5. customover magnesium sulfate and evaporation
  6. customgives an oil which
  7. customis crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-d778d248b0824f708e3b350749f01899
Source dataset
uspto-grants-1992_04
Patent number
US05102897

Reaction notes

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