Mercapto-ethanol → HCID 135484501, compound

HRID 744168Notes

Reaction equation

HRID 744168 reaction equation
C([O:9][C@H:10]1[C@@H:14]([O:15]C(=O)C2C=CC=CC=2)[C@H:13]([CH2:24][O:25]C(=O)C2C=CC=CC=2)[O:12][C@@H:11]1[N:34]1[CH:42]=[N:41][C:40]2[C:35]1=[N:36][C:37]([NH:44]C(=O)C)=[N:38][C:39]=2Cl)(=O)C1C=CC=CC=1.SC([OH:51])C.C[O-].[Na+]>C(O)(=O)C>[C@H:11]1([N:34]2[CH:42]=[N:41][C:40]3[C:39](=[O:51])[NH:38][C:37]([NH2:44])=[N:36][C:35]2=3)[O:12][C@@H:13]([CH2:24][OH:25])[C@H:14]([OH:15])[C@@H:10]1[OH:9]

Participants

5

Reactant 3

HCID 4713212Mercapto-ethanolHCID 10942334Sodium MethoxideHCID 53856178HCID 53856178, compound

Product 1

HCID 135484501HCID 135484501, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 12 (0.58 g, 0.88 mmol), mercaptoethanol (0.25 ml, 3.53 mmol) and NaOMe (0.76 ml, 3.53 mmol, 35% weight solution in MeOH (10 ml)) was refluxed for six hours. The reaction mixture was cooled, neutralized with glacial acetic acid and evaporated to dryness. The solid obtained was washed with CHCl3 and the residue was crystallized from water to yield pure 13 (0.215 g, 86%) as white crystal: m.p. 248° C. (dec).

Workup

  1. temperaturewas refluxed for six hours
  2. temperatureThe reaction mixture was cooled
  3. customevaporated to dryness
  4. customThe solid obtained
  5. washwas washed with CHCl3
  6. customthe residue was crystallized from water

Sources & evidence

ORD record
ord-4ee958872a1146909d78ff971e523222
Source dataset
uspto-grants-1996_09
Patent number
US05559101

Reaction notes

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