Dimethylformamide dimethyl acetal → ethyl (Z)-3-(dimethylamino)-2-[4-[(E)-dimethylaminomethylideneamino]-2-methylsulfanyl-1,3-thiazole-5-carbonyl]prop-2-enoate

HRID 16242Notes

Reaction equation

HRID 16242 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([S:15][CH3:16])[S:5][C:6]=1[C:7](=[O:14])[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].CO[CH:19](OC)[N:20]([CH3:22])[CH3:21]>C1(C)C=CC=CC=1>[CH3:19][N:20]([CH3:22])/[CH:21]=[C:8](/[C:7]([C:6]1[S:5][C:4]([S:15][CH3:16])=[N:3][C:2]=1/[N:1]=[CH:19]/[N:20]([CH3:22])[CH3:21])=[O:14])\[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 2807782Ethyl 3-(4-amino-2-methylthiothiazol-5-yl)-3-oxopropanoate

Product 1

HCID 13297627ethyl (Z)-3-(dimethylamino)-2-[4-[(E)-dimethylaminomethylideneamino]-2-methylsulfanyl-1,3-thiazole-5-carbonyl]prop-2-enoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of EXAMPLE 1A (8.8 g) and N,N-dimethyl-formamide dimethyl acetal (15.1 g) in toluene (170 mL) at 110° C. was stirred for 3 hours, concentrated to half volume, cooled, and filtered. 1H NMR (300 MHz, CDCl3) δ 8.40 (s, 1H), 7.42 (s, 1H), 3.99 (q, 2H), 3.05 (d, 6H), 2.92 (b, 6H), 2.65 (s, 3H), 1.04 (t, 3H).

Workup

  1. concentrationconcentrated to half volume
  2. temperaturecooled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-eddc73aee2034edd9b0b0809e72fd0fc
Source dataset
uspto-grants-2010_06
Patent number
US07737159B2

Reaction notes

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