Hydrochloric Acid → 4-(chloromethyl)-N-(2,4-dimethoxybenzyl)thiazol-2-amine

HRID 1685024Notes

Reaction equation

HRID 1685024 reaction equation
Cl.[Cl:2][CH2:3][C:4]1[N:5]=[C:6]([NH2:9])[S:7][CH:8]=1.[CH3:10][O:11][C:12]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:13]=1[CH:14]=O.CCN(C(C)C)C(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.C(O)(=O)C>[Cl:2][CH2:3][C:4]1[N:5]=[C:6]([NH:9][CH2:14][C:13]2[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:12]=2[O:11][CH3:10])[S:7][CH:8]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 691752,4-DimethoxybenzaldehydeHCID 732294-Chloromethylthiazol-2-ylamineHCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 866612894-(chloromethyl)-N-(2,4-dimethoxybenzyl)thiazol-2-amine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

The HCl salt of 4-(chloromethyl)thiazol-2-amine (10 mmol) was suspended in DCM (50 ml), and 2,4-dimethoxybenzaldehyde (1.0 eq. of) and DIEA (1.0 eq.) were added. To the mixture, acetic acid (1 ml) was added followed by addition of sodium triacetoxyborohydride (2.5 eq.) and the reaction was stirred at room temperature overnight. The reaction mixture was filtered through Celite and washed with DCM. The filtrate was concentrated and purified by column chromatography using 0-10% gradient of 7 N ammonia/MeOH and DCM to give 4-(chloromethyl)-N-(2,4-dimethoxybenzyl)thiazol-2-amine.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washwashed with DCM
  3. concentrationThe filtrate was concentrated
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-c2d99212943349bb8a321a652a9a77d7
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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