3-Amino-1,2-propanediol → HCID 14700208, compound

HRID 1651511Notes

Reaction equation

HRID 1651511 reaction equation
CO[C:3]([C:5]1[S:9][C:8]2[S:10][C:11]([S:13]([NH2:16])(=[O:15])=[O:14])=[CH:12][C:7]=2[CH:6]=1)=[O:4].[OH:17][CH:18]([CH2:21][OH:22])[CH2:19][NH2:20]>CO>[OH:17][CH:18]([CH2:21][OH:22])[CH2:19][NH:20][C:3]([C:5]1[S:9][C:8]2[S:10][C:11]([S:13]([NH2:16])(=[O:14])=[O:15])=[CH:12][C:7]=2[CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 735613-Amino-1,2-propanediolHCID 14700202Methyl 5-sulfamoylthieno[2,3-b]thiophene-2-carboxylate

Product 1

HCID 14700208HCID 14700208, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Methoxycarbonylthieno[2,3-b]thiophene-2-sulfonamide (0.83 g., 3 mmoles) and 2,3-dihydroxypropylamine (1.37 g., 15 mmoles) were dissolved in hot methanol and refluxed for 48 hours. The reaction was worked up by evaporating the methanol in vacuo. Water (7 mL) was added followed by the dropwise addition of conc. HCl until strongly acidic (~1.8 pH). The product crystallized out and was collected, washed with water and dried to give 0.90 g of crude product. Recrystallization from nitromethane gave 0.73 g of 5-(N-2,3-dihydroxypropylcarbamoyl)thieno[2,3-b]thiophene-2-sulfonamide, m.p. 117°-118° C.

Workup

  1. temperaturerefluxed for 48 hours
  2. customby evaporating the methanol in vacuo
  3. additionWater (7 mL) was added
  4. additionfollowed by the dropwise addition of conc. HCl until strongly acidic (~1.8 pH)
  5. customThe product crystallized out
  6. customwas collected
  7. washwashed with water
  8. customdried
  9. customto give 0.90 g of crude product
  10. customRecrystallization from nitromethane

Sources & evidence

ORD record
ord-7d9fc4a3d30a4aed8c45720ed3f55aad
Source dataset
uspto-grants-1990_05
Patent number
US04929549

Reaction notes

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