Ethanolamine → HCID 13883782, compound

HRID 543752Notes

Reaction equation

HRID 543752 reaction equation
[F:1][C:2]([F:24])([F:23])[CH2:3][N:4]=[C:5]([NH2:22])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([S:13][CH2:14][CH2:15][CH2:16][C:17]([O:19]CC)=O)[N:8]=1.[CH2:25]([CH2:27][NH2:28])[OH:26]>CO>[OH:26][CH2:25][CH2:27][NH:28][C:17](=[O:19])[CH2:16][CH2:15][CH2:14][S:13][C:9]1[N:8]=[C:7]([NH:6][C:5]([NH2:22])=[N:4][CH2:3][C:2]([F:1])([F:23])[F:24])[CH:12]=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 20202857HCID 20202857, compound

Product 1

HCID 13883782HCID 13883782, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethyl 4-[4-(2-[2,2,2-trifluoroethyl]guanidino)pyrimid-2-ylthio]butyrate (0.2 g.), ethanolamine (0.5 ml.) and MeOH (5 ml.) was heated under reflux for 48 hours and then evaporated to dryness. Water was added to the residue, and the mixture extracted with EtOAc. The extract was dried and evaporated to dryness and the residue recrystallised from a small volume of EtOAc to give N-(2-hydroxyethyl)-4-[4-(2-[2,2,2-trifluoroethyl]guanidino)pyrimid-2-ylthio]butyramide (0.12 g.), m.p. 148°-150°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 48 hours
  3. customevaporated to dryness
  4. additionWater was added to the residue
  5. extractionthe mixture extracted with EtOAc
  6. customThe extract was dried
  7. customevaporated to dryness
  8. customthe residue recrystallised from a small volume of EtOAc

Sources & evidence

ORD record
ord-d69676920811443d8679b5f80f17b6c1
Source dataset
uspto-grants-1984_05
Patent number
US04447441

Reaction notes

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