Hydrochloric Acid → HCID 18953921, compound

HRID 1491884Notes

Reaction equation

HRID 1491884 reaction equation
[NH2:1][C:2](=[N:4][C:5]1[S:6][CH:7]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16](OC)=[O:17])[N:11]=2)[N:9]=1)[NH2:3].[BH4-].[Na+].CO.Cl>O1CCCC1.O.C(OCC)(=O)C>[NH2:1][C:2](=[N:4][C:5]1[S:6][CH:7]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][OH:17])[N:11]=2)[N:9]=1)[NH2:3]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 18953773HCID 18953773, compound

Product 1

HCID 18953921HCID 18953921, compoundYield 90.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2-(diaminomethyleneamino)-4-(6-methoxycarbonylpyridin-2-yl)thiazole (0.7 g) and sodium borohydride (0.3 g) in tetrahydrofuran (10 ml) was added a methanol (1.5 ml) at 50°-55° C. and the mixture was stirred for 1.6 hours at the same temperature. The reaction mixture was added to a mixture of tetrahydrofuran, ethyl acetate and water and the mixture was adjusted to pH 9.5 with 6N-hydrochloric acid. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo to give 2-(diaminomethyleneamino)-4-(6-hydroxymethylpyridin-2-yl)thiazole (0.57 g).

Workup

  1. washThe separated organic layer was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-c4741f48f11f4c1595b8dd858621dc82
Source dataset
uspto-grants-1994_12
Patent number
US05371097

Reaction notes

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