Water → 4-(N4-acetylsulfanilamido)thiazole

HRID 1578742Notes

Reaction equation

HRID 1578742 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][S:5][CH:6]=1.N1[CH:12]=[CH:11]C=CC=1.C([C:16]1[CH:25]=[C:24]([NH2:26])[CH:23]=[CH:22][C:17]=1[S:18](Cl)(=[O:20])=[O:19])(=O)C.[OH2:27]>>[C:11]([NH:26][C:24]1[CH:25]=[CH:16][C:17]([S:18]([NH:1][C:2]2[N:3]=[CH:4][S:5][CH:6]=2)(=[O:19])=[O:20])=[CH:22][CH:23]=1)(=[O:27])[CH3:12]

Participants

5

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 14009640Thiazol-4-amineHCID 18792301Acetylsulfanilylchlorid

Product 1

HCID 541797934-(N4-acetylsulfanilamido)thiazole

Procedure

A cold solution of 1.60 g. (0.016 mole) of 4-aminothiazole in 20 ml. of dry pyridine is treated with 4.0 g. (0.017 mole) of acetylsulfanilyl chloride in small portions over 15 minutes. The reaction is allowed to warm slowly to room temperature and stirring continued for about 2 days. The red solution is diluted slowly with 120 ml. of water and then cooled in an ice-bath for 11/2 hours. The crystalline precipitate is collected and washed with a small amount of cold dilute hydrochloric acid followed by several portions of water. The yield of the air-dried cream-colored product is 4.10 g. (86%) m.p. 231°-2°C.

Workup

  1. additionThe red solution is diluted slowly with 120 ml
  2. customThe crystalline precipitate is collected
  3. washwashed with a small amount of cold dilute hydrochloric acid

Sources & evidence

ORD record
ord-ddee14c50115403aa484b9b7be7c93ca
Source dataset
uspto-grants-1976_02
Patent number
US03939172

Reaction notes

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